HCID 54262103, compound → 3-[3-({Benzenesulfonyl-[3-(3,5-dichloro-phenyl)-propyl]-amino}-methyl)-phenyl]-propionic acid methyl ester

HRID 2300548Notes

Reaction equation

HRID 2300548 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:14][CH:15]=[CH:16][C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)[CH:7]=1>O=[Pt]=O.CO>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 54262103HCID 54262103, compound

Product 1

HCID 544188813-[3-({Benzenesulfonyl-[3-(3,5-dichloro-phenyl)-propyl]-amino}-methyl)-phenyl]-propionic acid methyl esterYield 100.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-[3-{benzenesulfonyl-[3-(3,5-dichlorophenyl)-allyl]-amino}-methyl)-phenyl]-propionic acid methyl ester of Step A (237 mg), PtO2 (30 mg), and MeOH was hydrogenated on a Parr shaker at 50 psi for 2 h. The catalyst was removed by filtration through Celite and the volatiles were removed in vacuo to provide the title compound (240 mg). 1H NMR (400 MHz, CDCl3) δ 7.82 (d, 2H), 7.76-7.50 (m, 3H), 7.23 (m, 1H), 7.07 (m, 4H), 6.74 (s, 2H), 4.26 (s, 2H), 3.64 (s, 3H), 3.09 (t, 2H), 2.90 (t, 2H), 2.56 (t, 2H), 2.37 (t, 2H), 1.56 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-fa10ccc9b7974130919e80fe302dcae9
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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