4-(3,4-Difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidine → (+)-2-Oxo-4-(3,4-difluorophenyl)-oxazolidine-3-carboxylic acid [2-(4-phenyl-4-methoxycarbonyl-cyclohexylamino)-ethyl]amide

HRID 1106659Notes

Reaction equation

HRID 1106659 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][O:12][C:11](=[O:14])[N:10]2[C:15]([O:17]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].CO[C:29]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:34][CH2:33][CH:32]([NH:35][CH2:36][CH2:37][NH2:38])[C:31](=C=O)[CH2:30]1>ClCCl>[C:41]1([C:29]2([C:11]([O:12][CH3:13])=[O:14])[CH2:30][CH2:31][CH:32]([NH:35][CH2:36][CH2:37][NH:38][C:15]([N:10]3[CH:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=4)[CH2:13][O:12][C:11]3=[O:14])=[O:17])[CH2:33][CH2:34]2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 220490874-(3,4-Difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidineHCID 867553642-[4-Methoxy-carbonyl-4-phenylcyclohex-1-yl]aminoethylamine

Product 1

HCID 54253775(+)-2-Oxo-4-(3,4-difluorophenyl)-oxazolidine-3-carboxylic acid [2-(4-phenyl-4-methoxycarbonyl-cyclohexylamino)-ethyl]amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3,4-difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidine (50 mg, 0.123 mmol) and 2-[4-methoxy-carbonyl-4-phenylcyclohex-1-yl]aminoethylamine (75 mg) in dichloromethane (6 mL) was stirred at room temperature and the product formed was purified by preparative TLC on silica gel using ethyl acetate as the eluent. There were two bands for the two isomers, the higher band was the minor product (1H-NMR confirmed it to be the cis isomer with respect to methoxycarbonyl and amine groups) and the lower band was the major product (1H-NMR confirmed it to be the trans isomer with respect to methoxycarbonyl and amine groups). The HCl salt was made by treatment with 1N HCl in ether.

Workup

  1. customthe product formed
  2. customwas purified by preparative TLC on silica gel

Sources & evidence

ORD record
ord-943328a652e346b4878e57f5ae479487
Source dataset
uspto-grants-2000_05
Patent number
US06057350

Reaction notes

Loading…