Triethylamine → (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732596Notes

Reaction equation

HRID 732596 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13]CC(=O)C(C)(C)C)[CH2:10][C@@H:9]1[C@H:21]1[O:25][C:24]([CH3:27])([CH3:26])[N:23]([C:28](=[O:30])[CH3:29])[C@H:22]1[CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[CH2:10][C@@H:9]1[C@H:21]1[O:25][C:24]([CH3:26])([CH3:27])[N:23]([C:28](=[O:30])[CH3:29])[C@H:22]1[CH2:31][C:32]1[CH:33]=[C:34]([F:39])[CH:35]=[C:36]([F:38])[CH:37]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 68817555(2R,4R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(3,3-dimethyl-2-oxo-butoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68814480(R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl esterYield 95.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add sulfur trioxide pyridine complex (1.99 g, 12.46 mmol) to a solution of (2R,4R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(3,3-dimethyl-2-oxo-butoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.83 g, 6.23 mmol) and triethylamine (3.5 mL, 24.9 mmol) in dimethyl sulfoxide (14 mL) at 10° C. Stir 50 minutes, dilute with ethyl acetate and wash with water, saturated aqueous sodium chloride, dry with magnesium sulfate. Purify on silica gel with dichloromethane/ethyl acetate mixtures to give the desired compound as a foam (2.69 g, 95%).

Workup

  1. washwash with water, saturated aqueous sodium chloride
  2. dry with materialdry with magnesium sulfate
  3. customPurify on silica gel with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-cdb047fc590e4e4e8583998391b6cc85
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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