Dicyclohexylcarbodiimide → HCID 54337559, compound

HRID 893978Notes

Reaction equation

HRID 893978 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[NH:9][CH2:8][CH2:7][S:6]1)=[O:4].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[C:35]([S:38][CH2:39][CH:40]([CH3:44])[C:41](O)=[O:42])(=[O:37])[CH3:36]>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[N:9]([C:41](=[O:42])[CH:40]([CH3:44])[CH2:39][S:38][C:35](=[O:37])[CH3:36])[CH2:8][CH2:7][S:6]1)=[O:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1180733-(Acetylthio)-2-methylpropanoic acidHCID 2737507HCID 2737507, compound

Product 1

HCID 54337559HCID 54337559, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Thiazolidinecarboxylic acid methyl ester (C.A. 53, 12, 281) (4.4 g.) and 3-hydroxybenzotriazole (4.0 g.) are dissolved in dichloromethane (40 ml.) and the solution is stirred and chilled in an ice bath. Dicyclohexylcarbodiimide (6.2 g.) dissolved in dichloromethane (15 ml.) is added followed immediately by a solution of 3-acetylthio-2-methylpropanoic acid (4.9 g.) in dichloromethane (5 ml.). After fifteen minutes stirring in the ice bath, and sixteen hours at room temperature, the precipitate is filtered off and the filtrate is washed neutral. The organic layer is dried and concentrated to dryness in vacuo to give 3-(3-acetylthio-2-methylpropanoyl)-2-thiazolidinecarboxylic acid methyl ester.

Workup

  1. temperaturechilled in an ice bath
  2. additionis added
  3. filtrationthe precipitate is filtered off
  4. washthe filtrate is washed neutral
  5. customThe organic layer is dried
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d6352e54e281439fbbcdcd84f3792584
Source dataset
uspto-grants-1981_08
Patent number
US04282235

Reaction notes

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