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

HRID 1860100Notes

Reaction equation

HRID 1860100 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16](OS(C)(=O)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 18625936Ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate

Product 1

HCID 18625698Ethyl 3-(4-benzyloxyphenyl)-2-(phenylamino)propionate

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate (4.00 g) and aniline (5 ml) was stirred at 110° C. for 24 hours. The reaction mixture was purified via chromatography on silica gel column using ethyl acetate/hexane=1/4 as the eluant to afford the desired compound (3.94 g) as a syrup.

Workup

  1. customThe reaction mixture was purified via chromatography on silica gel column

Sources & evidence

ORD record
ord-3f2094485afa45ca803244feda02900c
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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