Dicyclohexylcarbodiimide → Carboxy methyl-t-butyl disulfide glycyl glycine t-butyl ester

HRID 452334Notes

Reaction equation

HRID 452334 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[NH2:16][CH2:17][C:18]([NH:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19].[CH3:29][CH2:30][C:31]([S:34][S:35][C:36]([OH:38])=[O:37])([CH3:33])[CH3:32]>C(Cl)Cl>[C:25]([O:24][C:22](=[O:23])[CH2:21][NH:20][C:18](=[O:19])[CH2:17][NH2:16])([CH3:28])([CH3:26])[CH3:27].[CH3:29][CH2:30][C:31]([S:34][S:35][C:36]([OH:38])=[O:37])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 15403805Tert-butyl 2-(2-aminoacetamido)acetateHCID 23071082Carboxy methyl-t-butyl disulfide

Product 1

HCID 86603847Carboxy methyl-t-butyl disulfide glycyl glycine t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 23.85 g (115.6 mmol) DCC in 430 ml CH2Cl2 was dropwise added to a solution of 21.76 g (115.6 mmol) Gly-Gly-O-tBu, 20.84 g (115.6 mmol) Carboxy methyl-t-butyl disulfide and 13.3 g (115.6 mmol) NHS in 1 l CH2Cl2. The resulting suspension was stirred over night under N2-atmosphere at room temperature. After filtration the resulting solution was washed 3× with 400 ml half-saturated aqueous NaHCO3 and 1× with 400 ml water. The dried organic layer (MgSO4) was evaporated under reduced pressure. The crude product was purified by chromatography on silica gel using a solvent gradient ranging from CH2Cl2/MeOH 99:1 to CH2Cl2/MeOH 98.5:1.5. 26.1 g (64%) were isolated as a yellow oil.

Workup

  1. filtrationAfter filtration the resulting solution
  2. washwas washed 3× with 400 ml half-saturated aqueous NaHCO3 and 1× with 400 ml water
  3. customThe dried organic layer (MgSO4) was evaporated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel using a solvent gradient
  5. custom26.1 g (64%) were isolated as a yellow oil

Sources & evidence

ORD record
ord-b119a4c5f39a4d408bc9b28bca1774a7
Source dataset
uspto-grants-2013_07
Patent number
US08491906B2

Reaction notes

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