Propylene Oxide → (4S)-4-Benzyl-1,3-thiazolidin-2-one

HRID 2410402Notes

Reaction equation

HRID 2410402 reaction equation
[CH2:1]([C@H:8]1[CH2:12][S:11][C:10](=S)[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1[O:17]C1C.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C@H:8]1[CH2:12][S:11][C:10](=[O:17])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 6422Trifluoroacetic acidHCID 11458470(S)-4-Benzylthiazolidine-2-thione

Product 1

HCID 25417901(4S)-4-Benzyl-1,3-thiazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4S)-4-benzyl-1,3-thiazolidine-2-thione (38 g) in dichloromethane (350 mL) cooled to 0° C., propylene oxide (12.7 mL) and trifluoroacetic acid (14 mL) were added. After stirring the reaction mixture for 2 hours, the solvents were evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 20% ethyl acetate in hexane as eluant to afford the title compound (0.9 g).

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customto obtain a residue which
  3. customwas purified by column chromatography over silica gel using 20% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-2998340a914f4bcfa5c46024cc9549c1
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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