Glycylglycylglycine → S-acetylmercaptoacetylglycylglycylglycine

HRID 2182215Notes

Reaction equation

HRID 2182215 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-fb4126f36a114054af88309d7e96599f
Source dataset
uspto-grants-2005_05
Patent number
US06897209B2

Reaction notes

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