Glycine → HCID 20515728, compound

HRID 1902532Notes

Reaction equation

HRID 1902532 reaction equation
[C:1]1([C:6]([CH:8]([CH3:12])[C:9](O)=[S:10])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][CH2:14][C:15]([OH:17])=[O:16].C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O>[C:1]1([C:6]([CH:8]([CH3:12])[C:9]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[S:10])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 10868DicyclohexylcarbodiimideHCID 178458558HCID 178458558, compound

Product 1

HCID 20515728HCID 20515728, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 21.6 g (0.1 mole) of 2-(2-thenoyl) thiopropionic acid and 7.5 g (0.1 mole) of glycine in 100 ml of dimethylsulfoxide, 20.6 g of N,N'-dicyclohexyl-carbodiimide are added, under stirring, between 15° to 20° C. Stirring is continued for half an hour more, most of the solvent is evaporated under vacuum, 200 ml of water are added and the solution is taken to pH 9 with NaOH. Dicyclohexylurea is eliminated by filtration, then it is acidified with HCl. 14.2 g (yield 52%) of N-[2-(2-thenoyl)thiopropionyl]-glycine are obtained. The product is unitary in TLC.

Workup

  1. stirringStirring
  2. waitis continued for half an hour
  3. custommore, most of the solvent is evaporated under vacuum, 200 ml of water
  4. additionare added
  5. filtrationDicyclohexylurea is eliminated by filtration

Sources & evidence

ORD record
ord-10321a70227846d283f2adf1c9358704
Source dataset
uspto-grants-1982_12
Patent number
US04363920

Reaction notes

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