Retrosynthesis in the manufacture of generic drugs : selected case studies /: selected case studies. (2021)
- Record Type:
- Book
- Title:
- Retrosynthesis in the manufacture of generic drugs : selected case studies /: selected case studies. (2021)
- Main Title:
- Retrosynthesis in the manufacture of generic drugs : selected case studies
- Further Information:
- Note: Pedro Paulo Santos, William Heggie.
- Authors:
- Santos, Pedro Paulo
Heggie, William - Contents:
- Preface XV A note about the book and its use XVII Abbreviations XIX 1 Introduction 1 2 GABAPENTIN 5 2.1 Worldwide sales and patent status 6 2.2 Gabapentin structure and general retrosynthetic strategy 7 2.3 The first reported synthesis of gabapentin 13 2.4 The evolution of the chemical synthesis of gabapentin 14 2.5 Strategy comparison and conclusions 28 2.6 Lessons from the gabapentin case 29 2.7 Reaction conditions for schemes A to D 31 2.8 References 34 3 CLOPIDOGREL 39 3.1 Worldwide sales and patent status 40 3.2 Clopidogrel structure and general retrosynthetic strategy 41 3.3 The first reported synthesis of Clopidogrel 49 3.4 The evolution of chemical synthesis of Clopidogrel 50 3.5 Strategy comparison and conclusions 71 3.6 Lessons from the Clopidogrel case 73 3.7 Reaction conditions for schemes C to J 73 3.8 References 78 4 CITALOPRAM AND ESCITALOPRAM 85 4.1 Worldwide sales and patent status 86 4.2 Escitalopram/Citalopram structure 87 4.3 Retrosynthetic analysis of Citalopram 88 4.4 Escitalopram retrosynthesis 93 4.5 The first reported synthesis of Citalopram 95 4.6 The evolution of chemical synthesis of Citalopram 96 4.7 A quick glimpse of Escitalopram 97 4.8 The two Grignard phase in Citalopram synthesis 98 4.9 The phthalane route—alkylation of a phthalane with an electrophilic side chain 107 4.10 Other synthetic routes to Citalopram 112 4.11 Strategy comparison and conclusions for the synthesis of Citalopram 113 4.12 The evolution of Escitalopram synthesis 113 4.13Preface XV A note about the book and its use XVII Abbreviations XIX 1 Introduction 1 2 GABAPENTIN 5 2.1 Worldwide sales and patent status 6 2.2 Gabapentin structure and general retrosynthetic strategy 7 2.3 The first reported synthesis of gabapentin 13 2.4 The evolution of the chemical synthesis of gabapentin 14 2.5 Strategy comparison and conclusions 28 2.6 Lessons from the gabapentin case 29 2.7 Reaction conditions for schemes A to D 31 2.8 References 34 3 CLOPIDOGREL 39 3.1 Worldwide sales and patent status 40 3.2 Clopidogrel structure and general retrosynthetic strategy 41 3.3 The first reported synthesis of Clopidogrel 49 3.4 The evolution of chemical synthesis of Clopidogrel 50 3.5 Strategy comparison and conclusions 71 3.6 Lessons from the Clopidogrel case 73 3.7 Reaction conditions for schemes C to J 73 3.8 References 78 4 CITALOPRAM AND ESCITALOPRAM 85 4.1 Worldwide sales and patent status 86 4.2 Escitalopram/Citalopram structure 87 4.3 Retrosynthetic analysis of Citalopram 88 4.4 Escitalopram retrosynthesis 93 4.5 The first reported synthesis of Citalopram 95 4.6 The evolution of chemical synthesis of Citalopram 96 4.7 A quick glimpse of Escitalopram 97 4.8 The two Grignard phase in Citalopram synthesis 98 4.9 The phthalane route—alkylation of a phthalane with an electrophilic side chain 107 4.10 Other synthetic routes to Citalopram 112 4.11 Strategy comparison and conclusions for the synthesis of Citalopram 113 4.12 The evolution of Escitalopram synthesis 113 4.13 Best processes for Escitalopram 126 4.14 Lessons from the Citalopram/Escitalopram case 127 4.15 Reaction conditions for schemes A to H 128 4.16 References 135 5 SITAGLIPTIN 141 5.1 Worldwide sales and patent status 142 5.2 Sitagliptin structure and general retrosynthetic analysis 143 5.3 The first reported Sitagliptin synthesis 149 5.4 The search for an industrial synthesis for Sitagliptin 149 5.5 Strategy comparison and conclusions 184 5.6 Lessons from the Sitagliptin case 189 5.7 Reaction conditions for schemes A to J 191 5.8 References 200 6 EZETIMIBE 207 6.1 Worldwide sales and patent status 208 6.2 Ezetimibe structure and general retrosynthetic analysis 209 6.3 The first Ezetimibe syntheses 219 6.4 The search for an industrial synthesis of Ezetimibe 221 6.5 Comparison of strategies and conclusions 255 6.6 The best syntheses 259 6.7 Lessons from the Ezetimibe case 261 6.8 Reaction conditions for schemes A to M 262 6.9 References 269 7 MONTELUKAST 275 7.1 Worldwide sales and patent status 275 7.2 Montelukast structure and general retrosynthetic analysis 277 7.3 Retrosynthetic outline 279 7.4 The first reported Montelukast synthesis 282 7.5 The evolution of industrial chemical syntheses of Montelukast 283 7.6 Synthesis of the thiol side chain 297 7.7 Strategy comparison and conclusions 301 7.8 Lessons from the Montelukast case 305 7.9 Reaction conditions for schemes A to F 307 7.10 References 312 8 OSELTAMIVIR 319 8.1 Worldwide sales and patents status 320 8.2 Oseltamivir structure and general retrosynthetic analysis 321 8.3 The first reported Oseltamivir synthesis 331 8.4 Routes from shikimic acid or quinic acid 332 8.5 The supply problem 342 8.6 First non-shikimic or quinic acid synthetic routes 343 8.7 Synthesis of Oseltamivir from cyclohexadiene derivatives 344 8.8 Building the carboxylic ring of Oseltamivir by a Diels-Alder reaction 350 8.9 Oseltamivir ring by a [3, 3] sigmatropic rearrangement 360 8.10 Oseltamivir synthesis by a Michael addition-Horner-Wadsworth-Emmons cascade sequence 360 8.11 Aldol type condensations as key ring-forming step 365 8.12 Metathesis as key-ring forming step 365 8.13 Strategy comparison and conclusions 374 8.14 Lessons from the Oseltamivir case 378 8.15 Reaction conditions for schemes B to R 378 8.16 References 390 9 A Final Word 395 … (more)
- Publisher Details:
- Hoboken, NJ : John Wiley & Sons
- Publication Date:
- 2021
- Copyright Date:
- 2021
- Extent:
- 1 online resource (xxi, 409 pages), illustrations
- Subjects:
- 615.1
Generic drugs
Organic compounds -- Synthesis
Generic drugs
Organic compounds -- Synthesis
Electronic books - Languages:
- English
- ISBNs:
- 9781119155553
9781119155546
1119155541
9781119155560
1119155568 - Related ISBNs:
- 111915555X
9781119155539
1119155533 - Notes:
- Note: Description based on online resource; title from digital title page (viewed on February 15, 2021).
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- Legal Deposit; Only available on premises controlled by the deposit library and to one user at any one time; The Legal Deposit Libraries (Non-Print Works) Regulations (UK).
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- Restricted: Printing from this resource is governed by The Legal Deposit Libraries (Non-Print Works) Regulations (UK) and UK copyright law currently in force.
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- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library HMNTS - ELD.DS.571417
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- 04_033.xml