Water → HCID 53921609, compound

HRID 1781306Notes

Reaction equation

HRID 1781306 reaction equation
I[Si](C)(C)C.C(OC([N:13]1[C@H:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][S:15][CH:14]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O)(C)(C)C.O>C(Cl)(Cl)Cl>[CH2:25]([CH:14]1[NH:13][C@H:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][S:15]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 54011789HCID 54011789, compound

Product 1

HCID 53921609HCID 53921609, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

C tert-Butyl (2RS,4R)-2-benzyl-4-thiazolidinecarboxalate may be prepared in the following 11.8 cm3 of iodotrimethyl-silane are introduced slowly at a temperature in the region of 25° C. into a solution of 30.5 g of tert-butyl (4R)-3-tert-butoxycarbonyl-2-benzyl-4-thiazolidine-carboxylate (isomer A) in 250 cm3 of chloroform. The reaction mixture is stirred for 1 hour, and 10 cm3 of water are then added. The organic phase is separated and the aqueous phase is extracted with twice 20 cm3 of methylene chloride. The combined organic phases are washed with 100 cm3 of water and with 100 cm3 of saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure at 40° C. 25.0 g of tert-butyl (2RS,4R)-2-benzyl-4-thiazolidinecarboxylate are thereby obtained in the form of a yellow oil, which is used in the subsequent syntheses without further treatment.

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is extracted with twice 20 cm3 of methylene chloride
  3. washThe combined organic phases are washed with 100 cm3 of water and with 100 cm3 of saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-f5ef483caa0240adbbfeffbf134b4a0e
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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