Hydrochloric Acid → ethyl 2-({2-[(4R)-4-formyl-2-oxo-1,3-oxazolidin-3-yl]ethyl}thio)-1,3-thiazole-4-carboxylate

HRID 1888295Notes

Reaction equation

HRID 1888295 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][O:6][C:5](=[O:8])[N:4]1[CH2:9][CH2:10][S:11][C:12]1[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1.C(OCC)(=O)C.C(N(CC)CC)C.Cl>CS(C)=O>[CH:2]([C@H:3]1[CH2:7][O:6][C:5](=[O:8])[N:4]1[CH2:9][CH2:10][S:11][C:12]1[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1)=[O:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66858106ethyl 2-({2-[(4S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}thio)-1,3-thiazol-4-carboxylate

Product 1

HCID 86650055ethyl 2-({2-[(4R)-4-formyl-2-oxo-1,3-oxazolidin-3-yl]ethyl}thio)-1,3-thiazole-4-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the compound 4 (338 mg) in dimethylsulfoxide (3.40 mL)/ethyl acetate (6.80 mL) were added triethylamine (1.00 mL) and sulfur trioxide-pyridine complex (650 mg) at 10° C. and the solution was stirred at room temperature for 1 hour. To the reaction solution was added 1N hydrochloric acid and the solution was extracted with ethyl acetate. The organic layer was washed water and brine, dried over anhydrous sodium sulfate and concentrated to give the title compound (336 mg) having the following physical data. The compound was used in the next reaction without purification.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c3fecfe31d41473b92cfa64be0e78898
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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