Water → (R)-3-phenyl-2-(2-phenyl-benzofuran-5-ylmethoxycarbonylamino)-propionic acid

HRID 2120591Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-3-phenyl-2-(2-phenyl-benzofuran-5-ylmethoxy-carbonylamino)-propionic acid methyl ester 28 (0.7 g, 1.63 mmol) in THF (15 ml) and methanol (15 ml) was added a solution of lithium hydroxide (1 N) in water (2 ml, 2 mmol). The reaction mixture was heated at 50° C. for 6 hrs then left at room temperature overnight. The solvent was evaporated and water (20 ml) was added. The mixture was acidified with 1N HCl and ethyl acetate was added. The solid obtained after precipitation and evaporation of the solvent was purified by recrystallization to give about 0.35 g of (R)-3-phenyl-2-(2-phenyl-benzofuran-5-ylmethoxycarbonylamino)-propionic acid 29, mp. 172.8-173.5° C.

Workup

customThe solvent was evaporated
additionwater (20 ml) was added
additionwas added
customThe solid obtained
customafter precipitation and evaporation of the solvent
customwas purified by recrystallization

Sources & evidence

ORD record: ord-72333bf5380a47e39d3b5915346a9647
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693098B2

Reaction notes

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