[4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

Base Information

Chemical Name:[4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester
CAS No.:300865-86-5
Molecular Formula:C₃₃H₅₈F₂N₄O₈
Molecular Weight:676.842
Hs Code.:

Synonyms:[4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

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Chemical Property of [4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

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Technology Process of [4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

There total 7 articles about [4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester 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:

: 37736-82-6
(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

: 300865-86-5
[4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: HATU; Et₃N / CH₂Cl₂ / 3 h / 20 °C

2: LiAlH₄ / diethyl ether / 0.33 h

3: 64 percent / Zn / tetrahydrofuran / 0.5 h / Heating

4: LiOH / acetonitrile / 2 h

5: HATU; i-Pr₂NEt / dimethylformamide / 0 °C

6: TFA / CH₂Cl₂ / 1 h / 20 °C

7: HOBT; EDC / CH₂Cl₂

With lithium hydroxide; lithium aluminium tetrahydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Reformatsky reaction / 4: Hydrolysis / 5: Condensation / 6: acidolysis / 7: Condensation;
DOI:10.1021/jm000100f

Reference yield:

: 98105-42-1
(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

: 300865-86-5
[4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 64 percent / Zn / tetrahydrofuran / 0.5 h / Heating

2: LiOH / acetonitrile / 2 h

3: HATU; i-Pr₂NEt / dimethylformamide / 0 °C

4: TFA / CH₂Cl₂ / 1 h / 20 °C

5: HOBT; EDC / CH₂Cl₂

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Reformatsky reaction / 2: Hydrolysis / 3: Condensation / 4: acidolysis / 5: Condensation;
DOI:10.1021/jm000100f

Reference yield:

: 103322-58-3
ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate

: 300865-86-5
[4(S)-[[(N-tert-butoxycarbonyl)-L-valyl]amino-2,2-difluoro-5-cyclohexyl-3(R)-hydroxypentanoyl]-L-valyl]-L-isoleucine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: LiOH / acetonitrile / 2 h

2: HATU; i-Pr₂NEt / dimethylformamide / 0 °C

3: TFA / CH₂Cl₂ / 1 h / 20 °C

4: HOBT; EDC / CH₂Cl₂

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Hydrolysis / 2: Condensation / 3: acidolysis / 4: Condensation;
DOI:10.1021/jm000100f