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

Base Information

• Chemical Name: ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate
• CAS No.: 103322-58-3
• Molecular Formula: C₁₈H₃₁F₂NO₅
• Molecular Weight: 379.445
• Mol file: 103322-58-3.mol

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

Chemical Property of ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate

There total 5 articles about ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate 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: 64.0%

Ethyl bromodifluoroacetate (667-27-6) + (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate (103322-58-3)

Guidance literature:

With zinc; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1021/jm000100f

Reference yield: 17.0%

Ethyl bromodifluoroacetate (667-27-6) + (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate (103322-58-3) + ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(S)-hydroxypentanoate (103420-29-7)

Guidance literature:

With iodine; zinc; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1021/jm00079a001

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid (37736-82-6) → ethyl 4(S)-<(tert-butyloxycarbonyl)amino>-5-(cyclohexylmethyl)-2,2-difluoro-3(R)-hydroxypentanoate (103322-58-3)

Guidance literature:

Multi-step reaction with 3 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

With lithium aluminium tetrahydride; triethylamine; 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; 1: Condensation / 2: Reduction / 3: Reformatsky reaction;

DOI:10.1021/jm000100f

upstream raw materials:

Ethyl bromodifluoroacetate

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

(S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-N-methoxy-N-methylcyclohexanepropanamide

Downstream raw materials:

N-<(8-propyl-6-pyridin-3-yl-1,2,4-triazolo<4,3-a>pyrazin-3-yl)-acetyl>-(3R,4S)-4-amino-5-cyclohexyl-2,2-difluoro-3-oxopentanoic acid (S)-2-methylbutylamide

N-<(8-propyl-6-pyridin-3-yl-1,2,4-triazolo<4,3-a>pyrazin-3-yl)-acetyl>-(3R,4S)-4-amino-5-cyclohexyl-2,2-difluoro-3-hydroxypentanoic acid (S)-2-methylbutylamide

(3R,4S)-4-Amino-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ((S)-2-methyl-butyl)-amide; hydrochloride

(S)-N-(4-morpholinylsulfonyl)-L-phenylalanyl-3-(2-amino-4-thiazolyl)-N-<1-(cyclohexylmethyl)-3,3-difluoro-4-<<2-(4-morpholinyl)ethyl>amino>-2,4-dioxobutyl>-L-alaninamide