tert-Butanol → N-((1S,3R,4S)-3-ethyl-4-isocyanatocyclopentyl)cyclopropanesulfonamide
Reaction equation
[CH:1]1([S:4]([NH:7][C@@H:8]2[CH2:12][C@H:11](C(O)=O)[C@H:10]([CH2:16][CH3:17])[CH2:9]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C1C=CC(P([N:32]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[C:36]([OH:39])(C)C>>[CH2:16]([C@H:10]1[C@@H:11]([N:32]=[C:36]=[O:39])[CH2:12][C@@H:8]([NH:7][S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:5])=[O:6])[CH2:9]1)[CH3:17]Participants
4
Conditions
- Temperature
- 70 °C
Procedure
To a mixture of (1S,2R,4S)-4-(cyclopropanesulfonamido)-2-ethylcyclopentanecarboxylic acid (Preparation #Z.1, 1.00 g, 3.83 mmol) in t-BuOH (19.1 mL) was added DPPA (0.826 mL, 3.83 mmol) and TEA (1.17 mL, 8.42 mmol). The reaction mixture was heated at about 70° C. for about 45 min. The reaction mixture was cooled to ambient temperature and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM. The material was dried under reduced pressure to give N-((1S,3R,4S)-3-ethyl-4-isocyanatocyclopentyl)cyclopropanesulfonamide with 30 mol % of t-BuOH as an excipient (0.97 g, 98%) as a colorless oil: LC/MS (Table 1, Method n) Rt=0.56 min; MS m/z 259 (M+H)+.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- customThe crude material was purified by silica gel chromatography
- washeluting with a gradient of 0-10% MeOH in DCM
- customThe material was dried under reduced pressure
Sources & evidence
- ORD record
- ord-2f571c76040148709eaf23e64829479e
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
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