tert-Butanol → N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide
반응식
[CH:1]1([S:4]([NH:7][CH:8]2[CH2:12][CH:11](C(O)=O)[CH:10]([CH3:16])[CH2:9]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C1C=CC(P([N:31]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[C:35]([OH:38])(C)C>>[N:31]([CH:11]1[CH:10]([CH3:16])[CH2:9][CH:8]([NH:7][S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:5])=[O:6])[CH2:12]1)=[C:35]=[O:38]참가 물질
4
반응 조건
- 온도
- 70 °C
실험 절차
To a solution of 4-(cyclopropanesulfonamido)-2-methylcyclopentanecarboxylic acid (4.10 g, 16.58 mmol, prepared from Example #24 Step I using Y, K, and Z) and DPPA (3.58 mL, 16.58 mmol) in t-BuOH (55 mL) was added TEA (5.0 mL, 36.5 mmol). The reaction was heated to about 70° C. for about 2 h then cooled to ambient temperature and concd under reduced pressure to afford a crude residue. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to afford N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide (3.25 g, 80%) as a white solid: LC/MS (Table 1, Method n) Rt=0.49 min; MS m/z: 245 (M+H)+.