L-Valine → 349-00-8
Reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].ClC(Cl)(Cl)[C:11]([C:13]([F:16])([F:15])[F:14])=[O:12]>CS(C)=O>[F:14][C:13]([F:16])([F:15])[C:11]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7.4 mmol of L-valine, 10 ml of dimethyl sulfoxide and 23 mmol of sym-trichlorotrifluoroacetone was stirred at room temperature for 24 hours in a flask protected from atmospheric moisture. A complete solution was obtained within the first hour. The progress of the reaction was followed by taking samples periodically and submitting them to gas-liquid chromatographic analysis. The reaction mixture was 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-trifluoroacetylvaline, melting at 88°-89° C., was obtained in a yield of 94 percent.
Workup
- customA complete solution was obtained within the first hour
- extractionthe resultant mixture was extracted thrice with n-butanol
- customchromatographed on a column
Sources & evidence
- ORD record
- ord-e3058d5873584c0fa457a5c7c45d8f8f
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03985723
Reaction notes
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