Sodium borohydride → N-[(3S)-3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxybutyl]-L-phenylalanyl-L-leucine, t-butyl ester

HRID 652341Notes

Reaction equation

HRID 652341 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:37])[C:10](=[O:36])[CH2:11][NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:37])[CH:10]([OH:36])[CH2:11][NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13633797N-[N-[(S)-3-[[(t-Butyloxy)carbonyl]amino]-2-oxobutyl]-L-phenylalanyl]-L-leucine, t-butyl ester

Product 1

HCID 13933328N-[(3S)-3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxybutyl]-L-phenylalanyl-L-leucine, t-butyl esterYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[N-[(S)-3-[[(t-butyloxy)carbonyl]amino]-2-oxobutyl]-L-phenylalanyl]-L-leucine, t-butyl ester (1.50 g, 2.89 mmol) in 15 ml of methanol at 0° C. was added sodium borohydride (109 mg, 2.89 mmol) in six portions over approximately 5 minutes. After 15 minutes, the solvent was evaporated. The residue was taken up into ethyl acetate (100 ml), washed with water until the extracts were neutral, washed with brine and then dried (sodium sulfate) and evaporated to give 1.41 g of the title compound as a mixture of diastereomers.

Workup

  1. customthe solvent was evaporated
  2. washwashed with water until the extracts
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-264f33165bbb4ba3b438acd3e77b4564
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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