Ethanol → Ethyl 3-(4-hydroxyphenyl)-2-(phenylamino)propionate

HRID 1871646Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)C>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

0.80 g of 5% palladium-carbon was added to a mixture of 3.94 g of ethyl 3-(4-benzyloxyphenyl)-2-(phenylamino)propionate obtained in Reference example 5(a), 40 ml of ethanol and 20 ml of tetrahydrofuran, and the mixture was stirred at 50° C. under hydrogen at normal pressure for 6 hours. The catalyst was removed by filtration from the reaction mixture, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 2.95 g of the desired compound as a syrup.

Workup

customThe catalyst was removed by filtration from the reaction mixture
customthe solvent was evaporated

Sources & evidence

ORD record: ord-fabe590d8c024dee9c08ad82b3061bf8
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103907

Reaction notes

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