Water → HCID 131714413, compound

HRID 652344Notes

Reaction equation

HRID 652344 reaction equation
Cl.[C:2]1([CH2:8][O:9][C:10]([NH:12][C@@H:13]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:14](=[O:35])[CH2:15][NH:16][C@H:17]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>O1CCCC1.O>[C:2]1([CH2:8][O:9][C:10]([NH:12][C@@H:13]([CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:14]([OH:35])[CH2:15][NH:16][C@H:17]([C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 131714414HCID 131714414, compound

Product 1

HCID 131714413HCID 131714413, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of N-[(3S)-3-[[(phenylmethoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]-L-phenylalanine, phenylmethyl ester, hydrochloride (2.12 g, 3.6 mmol) in 72 ml of 3:1 tetrahydrofuran-water was cooled to 0° C. Sodium borohydride (681 mg, 18 mmol) was added in approximately seven portions over 5-10 minutes. The reaction mixture was allowed to stir an additional 5 minutes and then poured into 150 ml of water. This mixture was extracted with 300 ml of ethyl acetate-ether (5:3). The organic extract was washed with water (2×50 ml) and brine (50 ml) and then dried (sodium sulfate) and evaporated to give 1.93 g of a colorless oil. This material was purified by flash chromatography on 150 g of Merck silica gel (230-400 mesh), eluting with hexane-ethyl acetate (1.25:1), to afford 1.14 g of the title compound as a white solid. The 13C-NMR spectrum was consistent with an approximately 2:1 mixture of alcohol diastereomers.

Workup

  1. extractionThis mixture was extracted with 300 ml of ethyl acetate-ether (5:3)
  2. extractionThe organic extract
  3. washwas washed with water (2×50 ml) and brine (50 ml)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-35ebe901f67442fab48be0ddccd5ecd7
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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