HCID 66654727, compound → HCID 66653911, compound
Reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@H:9]1[C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=O)(C)(C)C>C(Cl)Cl.Cl.O1CCOCC1>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][O:25][C:19]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=1[C@@H:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1)[CH3:31]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To an ice-cooled solution of (S)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (790 mg, 1.77 mmol, 1.0 eq.) in DCM (3 mL), 4M HCl in dioxane (7.4 mL) was added. The resulting solution was stirred at r.t. for 1.5 hours. The reaction mixture was concentrated in vacuo. The residue was coevaporated with EtOH (3×). To a solution of the residue in EtOH (2 mL), conc. H2SO4 (0.18 mL) was added. The solution was stirred at r.t. for 18 hours. Water and 5% aq. NaOH soln. were added and the mixture was extracted with Et2O (3×10 mL). The comb. org. phases were dried over MgSO4, filtered, and concentrated in vacuo to give the desired product.
Workup
- additionwas added
- concentrationThe reaction mixture was concentrated in vacuo
- additionTo a solution of the residue in EtOH (2 mL), conc. H2SO4 (0.18 mL) was added
- stirringThe solution was stirred at r.t. for 18 hours
- additionwere added
- extractionthe mixture was extracted with Et2O (3×10 mL)
- dry with materialphases were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-44e10bd7bd724c22b9a19e3c2e04f858
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575158B2
Reaction notes
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