methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

Base Information

Chemical Name:methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate
CAS No.:479480-66-5
Molecular Formula:C₂₉H₄₁F₂N₃O₆
Molecular Weight:565.658
Hs Code.:

Synonyms:methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

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Chemical Property of methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

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Technology Process of methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

There total 7 articles about methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: methyl N-[(3R)-3-amino-3-cyclohexyl-2,2-difluoropropanoyl]-L-phenylalaninate hydrochloride

: 15761-39-4,59433-50-0
1-(tert-butoxycarbonyl)-L-proline

: 479480-66-5
methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h; pH=8;
DOI:10.1021/jo0259313

Reference yield:

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 479480-66-5
methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole; Hunig's base / dimethylformamide / 18 h / 20 °C / pH 8

2: 77 percent / aq. HCl / diethyl ether / 18 h / 20 °C

3: 96 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole; Hunig's base / dimethylformamide / 18 h / 20 °C / pH 8

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo0259313

Reference yield:

: 2043-61-0
cyclohexanecarbaldehyde

: 479480-66-5
methyl N-((3R)-3-{[(1-tert-butoxycarbonyl)-L-prolyl]amino}-3-cyclohexyl-2,2-difluoropropanoyl)-L-phenylalaninate

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuSO₄; molecular sieves / CH₂Cl₂

2.1: Zn / tetrahydrofuran

2.2: tetrahydrofuran / 18 h / 20 °C

3.1: 48 percent / NaOH / ethanol / 18 h / 60 °C

4.1: 62 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole; Hunig's base / dimethylformamide / 18 h / 20 °C / pH 8

5.1: 77 percent / aq. HCl / diethyl ether / 18 h / 20 °C

6.1: 96 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole; Hunig's base / dimethylformamide / 18 h / 20 °C / pH 8

With hydrogenchloride; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; molecular sieve; copper(II) sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0259313