Dimethyl Sulfoxide → HCID 66848206, compound

HRID 536588Notes

Reaction equation

HRID 536588 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([OH:23])[CH2:20][C@H:19]1[CH2:24][O:25][C:26](=[O:36])[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)C(C)C)(C)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:22][C:21](=[O:23])[CH2:20][C@H:19]1[CH2:24][O:25][C:26](=[O:36])[C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 66848716HCID 66848716, compound2×

Product 1

HCID 66848206HCID 66848206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of oxalyl chloride (23.5 ml, 246 mmol) in dichloromethane (400 ml), which was cooled to −75° C., dimethyl sulfoxide (35 ml, 492 mmol) in dichloromethane (60 ml) was added in 20 minutes. After 30 minutes at −70° C., a solution of (2S,4R)-4-hydroxy-2-(4-nitro-benzoyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (intermediate 55, 45 g, 123 mmol) in dichloromethane (300 ml) was added dropwise. After 2 hours at −70° C., N,N-diisopropylethylamine (60 ml) was added in 10 minutes. After 25 minutes at −60° C. and 30 minutes at room temperature dichloromethane (200 ml) was added. The organic solvent was washed with 0.5N HCl (500 ml), water (500 ml) and brine (500 ml), dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 5/1 to 3/1). (S)-2-(4-Nitro-benzoyloxymethyl)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester was obtained as white solid (28.5 g, yield: 70%).

Workup

  1. waitAfter 2 hours at −70° C.
  2. waitAfter 25 minutes at −60° C.
  3. washThe organic solvent was washed with 0.5N HCl (500 ml), water (500 ml) and brine (500 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto obtain a crude that
  7. customwas purified by silica gel chromatography (petroleum ether/ethyl acetate from 5/1 to 3/1)

Sources & evidence

ORD record
ord-ea23213770f346ff9ce93d9d6a7dd987
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Reaction notes

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