Glycylglycylglycine → S-acetylmercaptoacetylglycylglycylglycine

HRID 480667Notes

Reaction equation

HRID 480667 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[O:4].FC1C([O:21][C:22](=O)[CH2:23][S:24][C:25](=[O:27])[CH3:26])=C(F)C(F)=C(F)C=1F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:25]([S:24][CH2:23][C:22]([NH:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[O:4])=[O:21])(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 11161GlycylglycylglycineHCID 81531DiisopropylethylamineHCID 3569623S-Acetylthioglycolic acid pentafluorophenyl ester

Product 1

HCID 14723672S-acetylmercaptoacetylglycylglycylglycine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of H-Gly-Gly-Gly-OH (1.28 g, 6.76 mmol), S-acetyl-thioglycolic acid pentafluorophenyl ester (Novabiochem, 2 g, 6.76 mmol) and DIPEA (1.14 ml, 6.76 mmol) in a mixture of DMF (25 ml) and water (12 ml), was stirred overnight at room temperature. The reaction mixture was filtered to remove some remaining H-Gly-Gly-Gly-OH, brought to pH2 with 1M aqueous HCl and evaporated to dryness. The residue was triturated with acetone to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove some remaining H-Gly-Gly-Gly-OH
  3. customevaporated to dryness
  4. customThe residue was triturated with acetone

Sources & evidence

ORD record
ord-8f40da1030bc4bd68750842dbd7161ca
Source dataset
uspto-grants-2003_11
Patent number
US06653299B1

Reaction notes

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