Trichloroisocyanuric Acid → (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 732381Notes

Reaction equation

HRID 732381 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[C@H:14]1[O:18][C:17]([CH3:20])([CH3:19])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]1[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[CH2:10][C@@H:9]1[C@H:14]1[O:18][C:17]([CH3:19])([CH3:20])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]1[CH2:24][C:25]1[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 68814386(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-hydroxypyrrolidine-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 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool to 0° C. a solution of (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.01 gr, 0.022 mmol) in dichloromethane (0.5 mL). Add trichloroisocyanuric acid (0.023 g, 0.110 mmol). Stir 5 minutes and then add TEMPO (2,2,6,6-tetramethyl-1-piperidinyl-oxy, free radical, 0.0007 g, 0.0044 mmol). After one hour add dichloromethane to the mixture and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound (0.010 g, 95%).

Workup

  1. washwash with saturated aqueous sodium bicarbonate
  2. dry with materialDry over magnesium sulfate
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-767cbb593110495cb8896e6e4f5553a6
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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