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

HRID 1860101Notes

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>[Pd].C(O)C.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

Palladium on carbon (5%, 0.80 g) was added to a solution of ethyl 3-(4-benzyloxyphenyl)-2-(phenylamino)propionate (3.94 g), which is the product of Reference example 55(a), in a mixture of ethanol (40 ml) and tetrahydrofuran (20 ml). The mixture was stirred under an atmosphere of hydrogen at 50° C. for 6 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified via chromatography on a silica gel column using ethyl acetate/hexane=1/2 as the eluant to afford the title compound (2.95 g) as a syrup.

Workup

customThe catalyst was removed by filtration
concentrationthe filtrate was concentrated
customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record: ord-31d3428611ff438a9b5fe1acf99514fa
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Reaction notes

Loading…