Lithium Hydroxide → 2-(S)-(2-benzyloxy-5-bromo-benzoylamino)-3-biphenyl-4-yl-propionic acid

HRID 2373841Notes

Reaction equation

HRID 2373841 reaction equation
C[O:2][C:3](=[O:36])[C@@H:4]([NH:18][C:19](=[O:35])[C:20]1[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[CH2:28]([O:27][C:21]1[CH:22]=[CH:23][C:24]([Br:26])=[CH:25][C:20]=1[C:19]([NH:18][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[C:3]([OH:36])=[O:2])=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 692063712-(S)-(2-Benzyloxy-5-bromo-benzoylamino)-3-biphenyl-4-yl-propionic acid methyl ester

Product 1

HCID 598525962-(S)-(2-benzyloxy-5-bromo-benzoylamino)-3-biphenyl-4-yl-propionic acidYield 69.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(S)-(2-Benzyloxy-5-bromo-benzoylamino)-3-biphenyl-4-yl-propionic acid methyl ester (50 mg, 0.092 mmol) was dissolved in 5 mL of THF-MeOH (4-1), cooled to 0° C. and 1.1 equiv of 2 N LiOH added. After 30 minutes, 3.3 additional equiv of 2N LiOH was added and the reaction stirred for 60 minutes. The reaction was worked up according to general procedure C to give 2-(S)-(2-benzyloxy-5-bromo-benzoylamino)-3-biphenyl-4-yl-propionic acid (34 mg)

Sources & evidence

ORD record
ord-0a7a4359c8c249c7950b6477cf847d7c
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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