Benzyl chloroformate → (R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

HRID 1722659Notes

Reaction equation

HRID 1722659 reaction equation
[S:1]1[CH2:5][C@@H:4]([C:6]([OH:8])=[O:7])[NH:3][CH2:2]1.[OH-].[Na+].[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([O:18][C:19]([N:3]1[C@H:4]([C:6]([OH:8])=[O:7])[CH2:5][S:1][CH2:2]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 93176L-Thioproline

Product 1

HCID 11119045(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acidYield 77.5%

Procedure

To a solution of 2.66 g of (R)-(-)-thiazolidine-4-carboxylic acid in 10 ml of a 2N-aqueous sodium hydroxide solution were added 4.1 g of benzyloxycarbonyl chloride and 15 ml of a 2N-aqueous sodium hydroxide solution with stirring under ice-cooling at the same time, and then the mixture was stirred for 2 hours at room temperature. The reaction mixture was washed with diethyl ether. The reaction mixture was then acidified by adding hydrochloric acid under ice-cooling. The mixture was allowed to stand for 30 minutes, and then the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to obtain 4.14 g of (R)-(-)-3-benzyloxycarbonylthiazolidine-4-carboxylic acid as a colorless clear viscous oil. The oily substance was allowed to stand under cooling to form a solid, and the solid was recrystallized from diethyl ether-petroleum ether to obtain a pure (R)-(-)-3-benzyloxycarbonylthiazolidine-4-carboxylic acid.

Workup

  1. temperaturecooling at the same time
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. washThe reaction mixture was washed with diethyl ether
  4. additionby adding hydrochloric acid under ice-
  5. temperaturecooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fc9fc109ca65481b8fe0d3befa7ef0ba
Source dataset
uspto-grants-1989_08
Patent number
US04857524

Reaction notes

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