Diethyl Ether → (R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

HRID 35864

Reaction equation

HRID 35864 reaction equation
[NH:1]1[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].CCOCC.[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[OH-].[Na+]>[CH2:14]([O:21][C:22]([N:1]1[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 93176L-Thioproline

Product 1

HCID 11119045(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

In 94 ml of 2-N NaOH was dissolved 25 g of L-thioproline, and 20 ml of ether was added to the solution under agitation and ice-cooling. To this solution under agitation were added dropwise 38 ml of benzyloxycarbonyl chloride and 70 ml of 4-N NaOH at the same time in 30 minutes. The mixture was stirred for 2 hours at room temperature, washed with 100 ml of ether and treated with 6-N HCl to adjust pH to 2. The mixture was extracted with 200 ml and 100 ml of ethyl acetate and the ethyl acetate phase was washed 50 ml of water, dried over MgSO4 and filtered. The filtrate was concentrated until dryness under reduced pressure whereby an oily substance was obtained.

Workup

  1. additionwas added to the solution under agitation and ice-
  2. temperaturecooling
  3. washwashed with 100 ml of ether
  4. additiontreated with 6-N HCl
  5. extractionThe mixture was extracted with 200 ml and 100 ml of ethyl acetate
  6. washthe ethyl acetate phase was washed 50 ml of water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated until dryness under reduced pressure whereby an oily substance
  10. customwas obtained

Sources & evidence

ORD record
ord-6a451b40f8a5463db5400fb49a3efa1b
Source dataset
uspto-grants-1995_05
Patent number
US05411976

Linked notes

Loading…