1-Chloroethyl chloroformate → HCID 66993654, compound
Reaction equation
C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([S:19][CH:20]([CH3:22])[CH3:21])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:23]C(OC(Cl)C)=O>C1(C)C=CC=CC=1>[ClH:23].[CH3:22][CH:20]([S:19][C:17]1[CH:16]=[N:15][C:13]2[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=2[N:18]=1)[CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 8-benzyl-3-[(1-methylethyl)sulfanyl]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (111 mg) in toluene (3 mL) was added 1-chloroethyl chloroformate (0.042 mL), and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was cooled to room temperature, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient; 3→40% ethyl acetate/hexane). To the obtained oil was added methanol (3 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to room temperature, and concentrated. The obtained residue was purified by recrystallization (ethanol-diisopropyl ether) to give the title compound (19.2 mg, 21%) as pale-yellow crystals.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated
- customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 3→40% ethyl acetate/hexane)
- additionTo the obtained oil was added methanol (3 mL)
- stirringthe mixture was stirred at 80° C. for 2 hr
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated
- customThe obtained residue was purified by recrystallization (ethanol-diisopropyl ether)
Sources & evidence
- ORD record
- ord-6f8838f972444b2cbe39b64be1a70cd2
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318722B2
Reaction notes
Loading…