HCID 24969814, compound → HCID 24969815, compound

HRID 604651Notes

Reaction equation

HRID 604651 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:29]([C:30]4[CH:35]=[C:34]([CH:36]([CH3:38])[CH3:37])[C:33]([F:39])=[CH:32][C:31]=4[O:40][CH3:41])=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[N+:42]([O-])=O)[CH:21]=3)[C@H:14]2[CH3:45])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>[Pd].CCOC(C)=O>[NH2:42][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[CH:28]=[C:29]([C:30]1[CH:35]=[C:34]([CH:36]([CH3:37])[CH3:38])[C:33]([F:39])=[CH:32][C:31]=1[O:40][CH3:41])[C:20]([CH2:19][N:15]1[C@@H:14]([CH3:45])[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:47])([F:1])[F:46])[CH:4]=3)[O:17][C:16]1=[O:18])=[CH:21]2

Participants

4

Reactant 1

HCID 24969814HCID 24969814, compound

Product 1

HCID 24969815HCID 24969815, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% palladium on carbon (4.0 mg) in a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[3-(4-fluoro-5-isopropyl-2-methoxyphenyl)-5-nitro-2-naphthyl]methyl}-4-methyl-1,3-oxazolidin-2-one (21.3 mg, 0.0321 mmol) in EtOAc (2.5 mL) was stirred under H2 (double balloon pressure) overnight. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford (4S,5R)-3-{[5-amino-3-(4-fluoro-5-isopropyl-2-methoxyphenyl)-2-naphthyl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one. LCMS calc.=635.2; found=634.8 (M+1)+.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-833dec7a2c674b26aae58e82e52b219b
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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