N-methyl-N-(trimethylsilyl)trifluoroacetamide → Acetic acid, 2,2,2-trifluoro-, trimethylsilyl ester
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].OC1C(O)=CC=CC=1C(NN)=O.CN([Si:28]([CH3:31])([CH3:30])[CH3:29])C(=O)C(F)(F)F>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([O:5][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
(2,3-Dihydroxybenzoyl)hydrazine, trifluoroacetate salt (2.82 g) was suspended in 50 ml of acetonitrile and 13.5 g of N-methyl-N-(trimethylsilyl)trifluoroacetamide were added. After stirring for one hour at 40° C., the solvent and trifluoroacetic acid, trimethylsilyl ester formed were distilled off in vacuo. The remaining oil was dissolved again in 50 ml of dried acetonitrile, cooled to 0° C. and added dropwise to a solution of 3.48 g of an adduct of chlorosulfonylisocyanate and (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 100 ml of acetonitrile at 0° C. with stirring. After continuous stirring overnight, the solvent was distilled off in vacuo and the residue stirred (1 hour) with 200 ml of isopropanol. (S)-3-[[(Phenylmethoxy)carbonyl]amino]-N-[[2-(2,3-dihydroxybenzoyl)hydrazino]sulfonyl]-2-oxo-1-azetidinecarboxamide precipitated from the solution. Isolation by filtration and washing with ether yielded 3.87 g of white powder.
Sources & evidence
- ORD record
- ord-d721a49d30144683abd852266ad7fa2c
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04801705
Reaction notes
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