HCID 11614252, compound → HCID 11592394, compound

HRID 1028579Notes

Reaction equation

HRID 1028579 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:35]=[C:34]([N+:36]([O-])=O)[CH:33]=[CH:32][C:31]=3[O:39][CH3:40])[C@H:14]2[CH3:41])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CCOC(C)=O.O=[Pt]=O>[NH2:36][C:34]1[CH:33]=[CH:32][C:31]([O:39][CH3:40])=[C:30]([C:21]2[CH:22]=[CH:23][C:24]([C:26]([F:28])([F:29])[F:27])=[CH:25][C:20]=2[CH2:19][N:15]2[C@@H:14]([CH3:41])[C@@H:13]([C:5]3[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:43])([F:1])[F:42])[CH:4]=3)[O:17][C:16]2=[O:18])[CH:35]=1

Participants

4

Reactant 1

HCID 11614252HCID 11614252, compound

Product 1

HCID 11592394HCID 11592394, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2′-methoxy-5′-nitro-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (example 122) (48.2 mg, 0.077 mmol) in EtOAc (4 mL) was added PtO2 (12 mg) and the reaction was placed under an atmosphere of hydrogen (balloon) and stirred vigorously. After 45 minutes, the catalyst was removed by filtration through a plug of silica gel with 100% EtOAc. The filtrate was concentrated to afford (4S,5R)-3-{[5′-amino-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.20 (40% EtOAc/hexanes). LCMS=593.2 (M+1)+. 1H NMR (CDCl3, 500 MHz, rotamers present) δ 7.85 (s, 1H), 7.60-7.70 (m, 4H), 7.36 (d, J=7.8 Hz, 1H), 6.74-6.84 (m, 2H), 6.56 (s, 1H), 5.45-5.54 (m, 1H), 4.82-4.87 (m, 1H), 3.64-4.17 (m, 2H), 3.70 (s, 3H), 0.43-0.53 (m, 3H).

Workup

  1. customthe catalyst was removed by filtration through a plug of silica gel with 100% EtOAc
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d04407425e3249c9ad34eda91c23fa08
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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