Sodium → S-acetylmercaptoacetylglycylglycylglycine

HRID 1723455Notes

Reaction equation

HRID 1723455 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[O:8])=[O:4].[C:18]([O-:21])(=[S:20])[CH3:19].[Na+].C(O)(=S)C.[Na]>CO>[C:18]([S:20][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[O:8])=[O:4])(=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 5360545SodiumHCID 14723669N-(Chloroacetyl)glycylglycylglycineHCID 23700354HCID 23700354, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 14723672S-acetylmercaptoacetylglycylglycylglycineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The crude chloroacetylglycylglycylglycine product (1.0 g, 0.0037 mol) was suspended in 50 ml of anhydrous methanol under nitrogen. Sodium thioacetate (prepared from 0.58 g (0.0076 mol) of thioacetic acid and dry methanol to which 175 mg (0.0076 mol) of sodium had been added) in methanol was added. The reaction mixture was refluxed for 1.5 hr. After removal of solvent under reduced pressure, 2N HCl was added with stirring. The solid was isolated by filtration and washed with CHCl3. Crystallization from methanol/water gave 1.00 g (90%) of product.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hr
  2. customAfter removal of solvent under reduced pressure, 2N HCl
  3. additionwas added
  4. customThe solid was isolated by filtration
  5. washwashed with CHCl3
  6. customCrystallization from methanol/water

Sources & evidence

ORD record
ord-70629e5f696b4ada9e247a1d9868df38
Source dataset
uspto-grants-1989_08
Patent number
US04861869

Reaction notes

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