Tert-Butylamine → 3-(benzyloxycarbonyl)-N-tert.butyl-4(R)-thiazolidinecarboxamide

HRID 54079Notes

Reaction equation

HRID 54079 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([OH:18])=O)[CH2:14][S:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[C:35]([NH2:39])([CH3:38])([CH3:37])[CH3:36]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([NH:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:18])[CH2:14][S:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 11119045(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

Product 1

HCID 186482733-(benzyloxycarbonyl)-N-tert.butyl-4(R)-thiazolidinecarboxamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of 2.67 g of N-benzyloxycarbonyl-4(R)-thiazolidinecarboxylic acid in 42 ml of dry tetrahydrofuran was stirred and cooled to -15° C. in an ice/salt bath while there were added 1.15 g of N-ethylmorpholine followed after 2 minutes by 1.87 g of isobutyl chloroformate. After a further 3 minutes 0.73 g of tert.butylamine was added dropwise and the mixture was then allowed to warm to room temperature and was stirred overnight. Tetrahydrofuran was removed by evaporation under reduced pressure and the residue was dissolved in dichloromethane. The solution was washed in sequence with water, 10% citric acid solution, water, saturated sodium bicarbonate solution and water, then dried over anhydrous sodium sulphate, filtered and evaporated to give 2.85 g of 3-(benzyloxycarbonyl)-N-tert.butyl-4(R)-thiazolidinecarboxamide as a solid which melted at 96°-98° C. after recrystallization from diethyl ether/n-hexane.

Workup

  1. temperatureto warm to room temperature
  2. customTetrahydrofuran was removed by evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe solution was washed in sequence with water, 10% citric acid solution, water, saturated sodium bicarbonate solution and water
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1f89d22ddfca4c4eb98f2b8f40ae0506
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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