Hydrochloric Acid → (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl N-(2-amino-2-methylcyclopentyl)carbamate hydrochloride
Reaction equation
C(OC([NH:8][C:9]1([CH3:28])[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:27])[O:16][C@@H:17]1[CH2:22][C@H:21]([CH3:23])[CH2:20][CH2:19][C@H:18]1[CH:24]([CH3:26])[CH3:25])=O)(C)(C)C.[ClH:29].O1CCOCC1>C(Cl)Cl>[ClH:29].[NH2:8][C:9]1([CH3:28])[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:27])[O:16][C@@H:17]1[CH2:22][C@H:21]([CH3:23])[CH2:20][CH2:19][C@H:18]1[CH:24]([CH3:25])[CH3:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl N-(2-{[(tert-butoxy)carbonyl]amino}-2-methylcyclopentyl)carbamate (25.2 g, 63.5 mmol) in DCM (100 ml) was added HCl in 1,4-dioxane (4 M, 60 ml, 240 mmol). The reaction mixture was stirred at room temperature for 18 hours and then further HCl in 1,4-dioxane (4 M, 20 ml, 80 mmol) was added and the stirred for an additional 24 hours at room temperature. The reaction was concentrated in vacuo and purified by SCX chromatography (2M ammonia in methanol). The resulting residue was suspended in DCM/methanol and to this was added HCl in 1,4-dioxane (4 M, 10 ml, 40 mmol) and stirred for 2 hours. The reaction was concentrated in vacuo and further evaporated from diethyl ether and then methanol to afford the title compound as a mixture of trans-amino compounds.
Workup
- stirringthe stirred for an additional 24 hours at room temperature
- concentrationThe reaction was concentrated in vacuo
- custompurified by SCX chromatography (2M ammonia in methanol)
- stirringstirred for 2 hours
- concentrationThe reaction was concentrated in vacuo
- customfurther evaporated from diethyl ether
Sources & evidence
- ORD record
- ord-c0f9ba5491d84a99a351650244997bcb
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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