Sodium borohydride → (3S)-N-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-L-phenylalanyl]-L-leucine, t-butyl ester

HRID 652359Notes

Reaction equation

HRID 652359 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[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]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[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])([CH3:34])[CH3:35])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131714427(3S)-N-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-L-phenylalanyl]-L-leucine, t-butyl ester

Product 1

HCID 131714428(3S)-N-[N-[3-[[(t-Butyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-L-phenylalanyl]-L-leucine, t-butyl esterYield 144.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3S)-N-[N-[3-[[(t-butyloxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-L-phenylalanyl]-L-leucine, t-butyl ester (1.46 g, 2.45 mmol) in 15 ml of methanol was cooled to 0° C. Sodium borohydride (93 mg, 2.45 mmol) was added in portions over 5 minutes. After 15 minutes, the solvent was evaporated. The residue was taken up into ethyl acetate (100 ml), washed with water, dried (sodium sulfate) and evaporated to give 1.14 g of a slightly yellow gum. This material was combined with 1.73 g of material similarly prepared. The combined material (2.87 g) was purified by flash chromatography on 215 g of Merck silica gel (230-400 mesh), eluting with hexane-ethyl acetate (1.5:1), to give 2.11 g of the title compound as a colorless oil; TLC: Rf =0.19, 1.25:1 hexane-ethyl acetate.

Workup

  1. customthe solvent was evaporated
  2. washwashed with water
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customto give 1.14 g of a slightly yellow gum
  6. customsimilarly prepared
  7. customThe combined material (2.87 g) was purified by flash chromatography on 215 g of Merck silica gel (230-400 mesh)
  8. washeluting with hexane-ethyl acetate (1.5:1)

Sources & evidence

ORD record
ord-aa301f38fd3e4779927008fec849d412
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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