Dichloromethane → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732602Notes

Reaction equation

HRID 732602 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13]CC2C=CC(OC)=CC=2)[CH2:10][C@@H:9]1[C@H:23]1[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:32])[CH3:31])[C@H:24]1[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[C:36]([F:41])[CH:35]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClCCl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[C@H:23]1[O:27][C:26]([CH3:28])([CH3:29])[N:25]([C:30](=[O:32])[CH3:31])[C@H:24]1[CH2:33][C:34]1[CH:35]=[C:36]([F:41])[CH:37]=[C:38]([F:40])[CH:39]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68816295(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68814386(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl esterYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of (2R,4R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (7.48 g, 13.0 mmol) in 20:1 dichloromethane:water (130 mL) add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (4.71 g, 20.74 mmol). Stir 4 h in an ice bath and wash with saturated aqueous sodium bicarbonate (3×300 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures) to give the title compound as a foam (5.288 g, 89%).

Workup

  1. washwash with saturated aqueous sodium bicarbonate (3×300 mL), saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. custompurify
  4. wash(silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-c4e226dd1ba34d3099c2d3d9b282a208
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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