반응 #64250

반응 방정식

(S)-pyroglutamic acid

triethylamine

pivaloyl chloride

trans-4-nitroxycyclohexylamine

triethylamine

→

N-(trans-4-nitroxycyclohexyl)-(S)-Pyroglutamic acid amide

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONone adds dropwise
2. 2
   workup.STIRRINGto stir for 2 d at room temperature
3. 3
   기타removes the solvent in a vacuum
4. 4
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
5. 5
   workup.STIRRINGshaken out with sodium hydrogen carbonate
6. 6
   건조After drying of the ethyl acetate phase with sodium sulphate
7. 7
   workup.DISTILLATIONdistilling off in a vacuum, trituration with ether and suction filtration, there

실험 절차

2.1 g (0.016 mol) (S)-pyroglutamic acid (2-pyrrolidinone-5-carboxylic acid) are dissolved in 50 ml abs. tetrahydrofuran and 2.5 ml (0.018 mol) triethylamine. With cooling to about 5° C., 2 ml (0.016 mol) pivaloyl chloride in 10 ml abs. tetrahydrofuran are added dropwise thereto. After 15 min stirring at 5° C., one adds dropwise thereto a solution of 3.9 g trans-4-nitroxycyclohexylamine in 40 ml abs. tetrahydrofuran and 2.8 ml (0.02 mol) triethylamine. Thereafter, one allows to stir for 2 d at room temperature, filters off with suction and removes the solvent in a vacuum. The residue is dissolved in ethyl acetate and shaken out with sodium hydrogen carbonate. After drying of the ethyl acetate phase with sodium sulphate, distilling off in a vacuum, trituration with ether and suction filtration, there remain 1.5 g of the title compound of the melting point 166° C., i.e. 35% of theory.

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