反应详情

Triethylamine (0.63 ml, 4.52 mmol) is added to a solution of 6-(benzyloxycarbonylamino)hexanoic acid (1.00 g, 3.77 mmol) in dimethylformamide (20 ml) and the mixture is left to stir at ambient temperature and under argon for 30 minutes. The solution is cooled to 0° C. and ethyl chloroformate (0.43 ml, 4.52 mmol) is added dropwise. After two hours at ambient temperature, N-hydroxysuccinimide (0.52 g, 4.52 mmol) is added and the mixture is left to stir overnight at ambient temperature. The mixture is evaporated to dryness before taking up the residue in water to which ethyl acetate is added. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated to dryness before purification on a silica gel column with an ethyl acetate/pentane mixture (75/25 v/v) as eluent. The fractions, once evaporated, give 1.13 g of succinimidyl 6(benzyloxycarbonylamino)hexanoate in the form of an oil.

1. waitthe mixture is left
2. temperatureThe solution is cooled to 0° C.
3. waitAfter two hours at ambient temperature
4. waitthe mixture is left
5. stirringto stir overnight at ambient temperature
6. customThe mixture is evaporated to dryness
7. additionis added
8. customThe phases are separated
9. extractionthe aqueous phase is extracted with ethyl acetate
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customevaporated to dryness before purification on a silica gel column with an ethyl acetate/pentane mixture (75/25 v/v) as eluent
13. customThe fractions, once evaporated