Dimethyl Sulfoxide → (S)-2,2-Dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

HRID 1261835Notes

Reaction equation

HRID 1261835 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]([N:21]1[C@@H:25]([CH2:26][CH2:27][OH:28])[CH2:24][O:23][C:22]1([CH3:30])[CH3:29])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[CH2:11]([O:18][C:19]([N:21]1[C@@H:25]([CH2:26][CH:27]=[O:28])[CH2:24][O:23][C:22]1([CH3:30])[CH3:29])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 60098506(S)-4-(2-Hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Product 1

HCID 60018412(S)-2,2-Dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethyl sulfoxide (6.39 g, 81.8 mmol) in DCM (25 mL) was added at −70° C. to a solution of oxalyl chloride (5.59 g, 44.1 mmol) in DCM (90 mL), then after 15 min a solution of (S)-4-(2-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (8.79 g, 31.5 mmol) in DCM (45 mL) was added dropwise. After 60 min Et3N (15.9 g, 157 mmol) was added, then after 20 min the cooling bath was removed and the reaction mixture was stirred for 2 h. The reaction mixture was poured onto water and extracted five times with DCM. The combined organic phases were dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 1:1) produced the title compound (8.52 g, 98%) as light yellow liquid.

Workup

  1. customafter 20 min the cooling bath was removed
  2. additionThe reaction mixture was poured onto water
  3. extractionextracted five times with DCM
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cf0a52e0de834710a39d78341aff7357
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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