Methyl propionate → 3-[3-({Benzenesulfonyl-[3-(3,5-dichloro-phenyl)-propyl]-amino}-methyl)-phenyl]-propionic acid

HRID 2117588Notes

Reaction equation

HRID 2117588 reaction equation
COC(=O)CC.C[O:8][C:9](=[O:40])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:20][CH:21]=[CH:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)[CH:13]=1>O=[Pt]=O.CO>[C:34]1([S:31]([N:19]([CH2:18][C:14]2[CH:13]=[C:12]([CH2:11][CH2:10][C:9]([OH:40])=[O:8])[CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)(=[O:33])=[O:32])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 11124Methyl propionateHCID 54262103HCID 54262103, compound

Product 1

HCID 183760973-[3-({Benzenesulfonyl-[3-(3,5-dichloro-phenyl)-propyl]-amino}-methyl)-phenyl]-propionic acidYield 103.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

3-[3-Benzenesulfonyl-[3-(3,5-dichloro-phenyl)-propyl]-amino}-methyl)-phenyl]-propionic acid methyl ester. A mixture 3-[3-({benzenesulfonyl-[3-(3,5-dichloro-phenyl)-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-9961922326dd4dd992bcc90f4151803e
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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