Sodium Azide → tert-butyl-{(4S)-5-azido-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate
반응식
CS(O[CH2:6][C@@H:7]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O>[C:15]([O:14][C:12](=[O:13])[NH:11][CH2:10][CH2:9][CH2:8][C@H:7]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][N:27]=[N+:28]=[N-:29])([CH3:18])([CH3:17])[CH3:16]참가 물질
4
반응 조건
- 온도
- 70 °C
실험 절차
A solution of 218 mg (0.55 mmol) of (2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl methanesulfonate (Example 84A) in 15 ml of dimethylformamide is mixed with 36 mg (0.55 mmol) of sodium azide and stirred at 70° C. for 12 h. Most of the solvent is removed by distillation in vacuo, and the residue is diluted with ethyl acetate. The mixture is washed several times with a saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness in vacuo. The product is reacted without further purification.