Methanol → (3R)-4-Amino-3-[4-chloro-2-(2-phenylethyl)phenyl]butanoic acid hydrochloride

HRID 1799191Notes

Reaction equation

HRID 1799191 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[C@@H:16]2[CH2:20][NH:19][C:18](=[O:21])[CH2:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[OH:23]>O=[Pt]=O>[ClH:15].[NH2:19][CH2:20][C@@H:16]([C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:17][C:18]([OH:21])=[O:23]

Participants

4

Reactant 2

HCID 887MethanolHCID 667249334-[2-((1E)-2-Phenylvinyl)-4-chlorophenyl](4R)pyrrolidin-2-one

Product 1

HCID 66724962(3R)-4-Amino-3-[4-chloro-2-(2-phenylethyl)phenyl]butanoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

Crude 4-[2-((1E)-2-phenylvinyl)-4-chlorophenyl](4R)pyrrolidin-2-one (3a) was then stirred overnight with 5% PtO2 in methanol under a hydrogen atmosphere (1 atm). The catalyst was filtered using Celite and filtrate concentrated to dryness. The crude product was treated overnight with 6N HCl aqueous solution at 90° C. and the title compound (3) purified by HPLC. 1H-NMR (400 MHz, CD3OD): δ 2.36-2.41 (dd, J=16.0, 4.0 Hz, 1H), 2.69-2.75 (dd, J=16.0, 8.0 Hz, 1H), 2.88-3.00 (m, 4H), 3.05-3.12 (m, 1H), 3.17-3.24 (m, 1H), 3.65-3.69 (m, 1H), 7.14-7.22 (m, 8H); MS (ESI) m/z 318.09 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationconcentrated to dryness
  3. additionThe crude product was treated overnight with 6N HCl aqueous solution at 90° C.
  4. customthe title compound (3) purified by HPLC

Sources & evidence

ORD record
ord-22778ea94fb443738795759b6bd4fbbb
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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