(N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide

Base Information

• Chemical Name: (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide
• CAS No.: 173918-65-5
• Molecular Formula: C₃₇H₅₁F₂N₅O₈
• Molecular Weight: 731.837
• Mol file: 173918-65-5.mol

Synonyms:(N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide

Chemical Property of (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide

There total 10 articles about (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide 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:

(R,S)-α-benzyloxycarbonylamino-3-(4-nitrophenyl)propanal (119860-38-7) → (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide (173918-65-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) zinc, iodine / 1.) THF, rt, 15 min, ultrasonication; 2.) THF, rt, 35 min, ultrasonication

2: 95 percent / ammonia gas / diethyl ether / -78 °C

3: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

4: trifluoroacetic acid / 1.5 h / 0 °C

5: N-methylmorpholine, isobutylchloroformate / acetonitrile; dimethylformamide / 15 h / -20 - 20 °C

6: 1.) tin(II) chloride dihydrate; 2.) H₂O / ethanol / 3 h / Heating

7: 0.68 g / sodium bicarbonate / ethanol; H₂O / 16 h / Ambient temperature

8: hydrogen / 10percent palladium on charcoal / ethanol / 12 h / 760 Torr / Ambient temperature

9: 1.) N-methylmorpholine, isobutylchloroformate / 1.) acetonitrile, -20 deg C, 15 min; 2.) acetonitrile, rt, 15 h

With 4-methyl-morpholine; hydrogenchloride; dimethylsulfide borane complex; ammonia; water; hydrogen; iodine; sodium hydrogencarbonate; sodium carbonate; trifluoroacetic acid; tin(ll) chloride; zinc; isobutyl chloroformate; palladium on activated charcoal; In diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

N1-Acetyl-N4-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-aminophenyl)-1,4-pentanediamine (119885-17-5) → (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide (173918-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.68 g / sodium bicarbonate / ethanol; H₂O / 16 h / Ambient temperature

2: hydrogen / 10percent palladium on charcoal / ethanol / 12 h / 760 Torr / Ambient temperature

3: 1.) N-methylmorpholine, isobutylchloroformate / 1.) acetonitrile, -20 deg C, 15 min; 2.) acetonitrile, rt, 15 h

With 4-methyl-morpholine; hydrogen; sodium hydrogencarbonate; isobutyl chloroformate; palladium on activated charcoal; In ethanol; water;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

[4-Amino-3,3-difluoro-2-hydroxy-1-(4-nitro-benzyl)-butyl]-carbamic acid benzyl ester (119860-09-2) → (N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide (173918-65-5)

Guidance literature:

Multi-step reaction with 5 steps

1: N-methylmorpholine, isobutylchloroformate / acetonitrile; dimethylformamide / 15 h / -20 - 20 °C

2: 1.) tin(II) chloride dihydrate; 2.) H₂O / ethanol / 3 h / Heating

3: 0.68 g / sodium bicarbonate / ethanol; H₂O / 16 h / Ambient temperature

4: hydrogen / 10percent palladium on charcoal / ethanol / 12 h / 760 Torr / Ambient temperature

5: 1.) N-methylmorpholine, isobutylchloroformate / 1.) acetonitrile, -20 deg C, 15 min; 2.) acetonitrile, rt, 15 h

With 4-methyl-morpholine; water; hydrogen; sodium hydrogencarbonate; tin(ll) chloride; isobutyl chloroformate; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4020(95)00896-G

upstream raw materials:

N-[(1,1-dimethylethoxy)carbonyl]-D-phenylalanyl-L-proline

[4-(5-Acetylamino-2-amino-4,4-difluoro-3-hydroxy-pentyl)-phenyl]-carbamic acid tert-butyl ester

(R,S)-α-benzyloxycarbonylamino-3-(4-nitrophenyl)propanal

[4-Amino-3,3-difluoro-2-hydroxy-1-(4-nitro-benzyl)-butyl]-carbamic acid benzyl ester