Dicyclohexylcarbodiimide → S-methyl-thioglycolic Acid-N-(2-methylthioethyl)-amide

HRID 2296587Notes

Reaction equation

HRID 2296587 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][NH2:5].[CH3:6][S:7][CH2:8][C:9](O)=[O:10].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][S:2][CH2:3][CH2:4][NH:5][C:9](=[O:10])[CH2:8][S:7][CH3:6]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 75551(Methylthio)acetic acidHCID 80170N-HydroxysuccinimideHCID 87697(2-(Methylthio)ethyl)amine

Product 1

HCID 18387078S-methyl-thioglycolic Acid-N-(2-methylthioethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6 ml of 2-methylthio-ethylamine is dissolved in 250 ml of methylene chloride, mixed with 6.84 g of S-methyl-thioglycolic acid and with 7.42 g of N-hydroxysuccinimide and mixed drop by drop with 13.3 g of dicyclohexylcarbodiimide in 250 ml of methylene chloride under a cover-gas atmosphere. It is stirred, for 3 more hours at room temperature. The precipitate is filtered off, the filtrate is washed twice with semi-saturated sodium bicarbonate solution and once with water, dried with sodium sulfate and concentrated by evaporation. The residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol: Yield 10 g=86.7% of theory.

Workup

  1. filtrationThe precipitate is filtered off
  2. washthe filtrate is washed twice with semi-saturated sodium bicarbonate solution and once with water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol

Sources & evidence

ORD record
ord-28b7090dc04a4b5398f0f5ee3b6792e1
Source dataset
uspto-grants-2002_12
Patent number
US06488909B1

Reaction notes

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