Dicyclohexylcarbodiimide → benzoylmercaptoacetyl-N-hydroxysuccinimide

HRID 342332

Reaction equation

HRID 342332 reaction equation
[C:1]([S:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14][N:15]1[C:19](=[O:20])[CH2:18][CH2:17][C:16]1=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[C:1]([S:9][CH2:10][C:11]([CH:17]1[CH2:18][C:19](=[O:20])[N:15]([OH:14])[C:16]1=[O:21])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 51165332-benzoylsulfanylacetic Acid

Product 1

HCID 86749986benzoylmercaptoacetyl-N-hydroxysuccinimideYield 78.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
4 °C

Procedure

To a stirring solution of (9.20 g, 46.9 mmoles) benzoylmercaptoacetic acid and (5.41 g, 46.9 mmoles) N-hydroxysuccinimide in (100 mL) dioxane was added a solution of (9.70 g, 47 mmoles) dicyclohexylcarbodiimide in (40 mL) dioxane. The reaction was stirred 12 hours followed by cooling to 4° C., filtering, and rotavapping off the dioxane to a white solid. The solid was triturated with cold isopropanol, filtered, and dried in vacuo yielding 10.8 g, 78% benzoylmercaptoacetyl-N-hydroxysuccinimide. 200 mg was recrystallized from 500 mg in hot ethyl acetate.

Workup

  1. filtrationfiltering
  2. customThe solid was triturated with cold isopropanol
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-145326acdd6f4ef8b5e17ee413bb8e2b
Source dataset
uspto-grants-1999_01
Patent number
US05858327

Linked notes

Loading…