Ethanol hydrochloride → HCID 53996312, compound
Reaction equation
C(OC([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:14][CH:15]=2)[CH2:10]1)=O)(C)(C)C.C(O)C.Cl>C(O)C>[NH2:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:14][CH:15]=2)[CH2:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl (S)-5-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]valerate (687 mg) was dissolved in ethanol (10 ml), and 3 M hydrogen chloride ethanol solution (3 ml) was added to the solution at room temperature with stirring. After reaction for 15 hours, the reaction mixture was concentrated in vacuo. A saturated aqueous sodium bicarbonate solution (10 ml) and dichloromethane (5 ml) were added to the residue, and the resulting mixture was stirred for an hour at room temperature. Water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave ethyl (S)-5-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yl)valerate (509 mg) as an oil.
Workup
- customAfter reaction for 15 hours
- concentrationthe reaction mixture was concentrated in vacuo
- additionA saturated aqueous sodium bicarbonate solution (10 ml) and dichloromethane (5 ml) were added to the residue
- stirringthe resulting mixture was stirred for an hour at room temperature
- additionWater was added to the reaction mixture
- extractionthe resulting mixture was extracted with dichloromethane
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customRemoval of the solvent in vacuo
Sources & evidence
- ORD record
- ord-7ef213afe6504b8c90b2a77977910fc7
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136852
Reaction notes
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