Hydrochloric Acid → N-((1S,3S,4R)-3-amino-4-ethylcyclopentyl)cyclopropanesulfonamide hydrochloride
Reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([N:8]=C=O)[CH2:6][C@@H:5]([NH:11][S:12]([CH:15]2[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH2:4]1)[CH3:2].[ClH:18].CCOCC.CCOC(C)=O>O>[ClH:18].[NH2:8][C@@H:7]1[C@H:3]([CH2:1][CH3:2])[CH2:4][C@H:5]([NH:11][S:12]([CH:15]2[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH2:6]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of N-((1S,3R,4S)-3-ethyl-4-isocyanatocyclopentyl)cyclopropanesulfonamide (0.972 g, 3.76 mmol) and aqueous HCl (6 N, 31.4 mL, 188 mmol) was heated at about 100° C. for about 60 h. Aqueous HCl (12 N, 5 mL) was added and the reaction mixture was heated at about 100° C. for about 18 h. The reaction mixture was cooled to ambient temperature and concd under reduced pressure. The residue was treated with Et2O (10 mL) and EtOAc (10 mL). The mixture was concd under reduced pressure. Water (5 mL) was added and the sample was lyophilized to give N-((1S,3S,4R)-3-amino-4-ethylcyclopentyl)cyclopropane-sulfonamide hydrochloride (0.859 g, 85%) as a white solid: LC/MS (Table 1, Method a) Rt=1.28 min; MS m/z 233 (M+H)+.
Workup
- temperaturethe reaction mixture was heated at about 100° C. for about 18 h
- temperatureThe reaction mixture was cooled to ambient temperature
Sources & evidence
- ORD record
- ord-7af389feb57d4fc985f1fe65bbe68caf
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
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