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

HRID 1583676Notes

Reaction equation

HRID 1583676 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-6a43bd46119a409a9acaf519be4c8230
Source dataset
uspto-grants-1985_11
Patent number
US04552866

Reaction notes

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