(R)-3-[(E)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-acryloyl]-4-benzyl-oxazolidin-2-one → (R)-3-[3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionyl]-4-benzyl-oxazolidin-2-one

HRID 736922Notes

Reaction equation

HRID 736922 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](/[CH:12]=[CH:13]/[C:14]([N:16]2[C@H:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][O:18][C:17]2=[O:28])=[O:15])=[CH:4][C:3]=1[Cl:29]>[Ni].CO>[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5]([CH2:12][CH2:13][C:14]([N:16]2[C@H:20]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:19][O:18][C:17]2=[O:28])=[O:15])=[CH:4][C:3]=1[Cl:29]

Participants

4

Reactant 1

HCID 68592504(R)-3-[(E)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-acryloyl]-4-benzyl-oxazolidin-2-one

Product 1

HCID 68590943(R)-3-[3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionyl]-4-benzyl-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 23.7 g (55.8 mmol) of (R)-3-[(E)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-acryloyl]-4-benzyl-oxazolidin-2-one, 400 mL of MeOH and 5.0 g of Raney nickel was shaken for 2 h at RT and 3 bar of H2 in a Parr autoclave. The catalyst was suction filtered and the solvent removed i. vac. The desired product was obtained in the form of a yellow oil.

Workup

  1. filtrationfiltered
  2. customthe solvent removed i

Sources & evidence

ORD record
ord-2fd596c9eefc404dbb89ae1d077921de
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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