HCID 58256418, compound → HCID 58256428, compound

HRID 1805241Notes

Reaction equation

HRID 1805241 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[C:15]([F:18])([F:17])[F:16])[CH2:11][O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[C:15]([F:18])([F:16])[F:17])[CH2:11][O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58256418HCID 58256418, compound

Product 1

HCID 58256428HCID 58256428, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of (S)-2,2-dimethyl-4-[(R)-3,3,3-trifluoro-2-(4-nitro-phenoxy)-propyl]-oxazolidine-3-carboxylic acid tert-butyl ester (2.66 g) in methanol (20 ml) was added 10% palladium on charcoal (326 mg) and the mixture was then stirred under an atmosphere of hydrogen at room temperature for 3 hours. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to afford (S)-4-[(R)-2-(4-amino-phenoxy)-3,3,3-trifluoro-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.80 g, 73%) as a yellow viscous oil. MS (ISP): 405.4 ([M+H]+), 349.3 ([M+H—C4H8]+), 305.3 ([M+H—C4H8—CO2]+).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c91ac0aee31a46428bd686e7874c1c3e
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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