Sodium borohydride → (3S)-1-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, t-butyl ester

HRID 1583681Notes

Reaction equation

HRID 1583681 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:10](=[O:39])[CH2:11][N:12]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[C@H:13]([C:15]([N:17]1[CH2:28][CH2:27][CH2:26][C@H:18]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:10]([OH:39])[CH2:11][N:12]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[C@H:13]([C:15]([N:17]1[CH2:28][CH2:27][CH2:26][C@H:18]1[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[O:16])[CH3:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131714417(3S)-1-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, t-butyl ester

Product 1

HCID 131714416(3S)-1-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, t-butyl esterYield 62.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3S)-1-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, t-butyl ester (1.75 g, 2.75 mmol) was dissolved in ethanol (15 ml), and stirred in an ice bath. Sodium borohydride (150 mg, 3.95 mmol) was added and the solution was stirred at room temperature for 90 minutes. It was then evaporated, taken into ethyl acetate and washed with 10% aqueous potassium hydrogen sulfate solution. The ethyl acetate solution after evaporation was chromatographed over silica gel (100 g) using the solvent system ethyl acetate:hexane-4:6 to obtain 1.1 g of the title compound.

Workup

  1. stirringthe solution was stirred at room temperature for 90 minutes
  2. customIt was then evaporated
  3. washwashed with 10% aqueous potassium hydrogen sulfate solution
  4. customThe ethyl acetate solution after evaporation
  5. customwas chromatographed over silica gel (100 g)

Sources & evidence

ORD record
ord-50ab8f05a78d4a9bb1473ff991cd53d3
Source dataset
uspto-grants-1985_11
Patent number
US04552866

Reaction notes

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