Sodium borohydride → N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

HRID 634945Notes

Reaction equation

HRID 634945 reaction equation
[C:1]([C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:43])[CH2:31][O:32][C:33]1[C:38]([F:39])=[C:37]([F:40])[CH:36]=[C:35]([F:41])[C:34]=1[F:42])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CO.C1COCC1.[BH4-].[Na+]>[NH4+].[Cl-]>[C:1]([C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([CH:30]([OH:43])[CH2:31][O:32][C:33]1[C:34]([F:42])=[C:35]([F:41])[CH:36]=[C:37]([F:40])[C:38]=1[F:39])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21899815MeOH tetrahydrofuranHCID 86584479N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Product 1

HCID 86584481N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

A solution of N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (6.18 g, 10.57 mmol) in 1:1 MeOH/THF (100 ml) was cooled to 0° C. and NaBH4 (1.20 g, 31.72 mmol) was added and stirred for 2 hours. The reaction was diluted with saturated NH4Cl and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the titled product as a white solid (6.14 g, 10.46 mmol, 98%). MS C28H34N2O7, [M+Na]+ =609, [M−H]−=585.

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e57e205cdf74c688933b985b59cedcf
Source dataset
uspto-grants-2001_02
Patent number
US06184244B2

Reaction notes

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