Glycylglycine → N-(N-(Trifluoroacetyl)glycylglycine

HRID 1287555Notes

Reaction equation

HRID 1287555 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4].ClC(Cl)(Cl)[C:12]([C:14]([F:17])([F:16])[F:15])=[O:13]>CS(C)=O>[F:15][C:14]([F:17])([F:16])[C:12]([NH:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4])=[O:13]

Participants

4

Reactant 2

HCID 11163GlycylglycineHCID 697961,1,1-Trichloro-3,3,3-trifluoroacetone

Product 1

HCID 136245N-(N-(Trifluoroacetyl)glycylglycineYield 42.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 7.85 mmol of glycylglycine, 15 ml of dimethyl sulfoxide and 24 mmol of sym-trichlorotrifluoroacetone was stirred at room temperature for 24 hours in a flask protected from atmospheric moisture. The reaction mixture was then poured into 50 ml of ice water and the resultant mixture was extracted thrice with n-butanol and chromatographed on a column packed with silica gel. N-trifluoroacetylglycylglycine, melting at 184.7°-185.0° C., was obtained in a yield of 42.5 percent.

Workup

  1. extractionthe resultant mixture was extracted thrice with n-butanol
  2. customchromatographed on a column

Sources & evidence

ORD record
ord-a00f3f0b4ab444318fae4cc9d0730ee3
Source dataset
uspto-grants-1976_10
Patent number
US03985723

Reaction notes

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