Acetyl chloride → HCID 66673333, compound
Reaction equation
C(Cl)(=O)C.C(OC(=O)[NH:11][C@H:12]1[C@H:21]([O:22][CH3:23])[CH2:20][C:19]2[C:14](=[CH:15][C:16]([C:24](=[O:26])[NH2:25])=[CH:17][CH:18]=2)[C:13]1([CH2:29][CH3:30])[CH2:27][CH3:28])(C)(C)C>C(O)C>[NH2:11][C@@H:12]1[C:13]([CH2:27][CH3:28])([CH2:29][CH3:30])[C:14]2[CH:15]=[C:16]([C:24]([NH2:25])=[O:26])[CH:17]=[CH:18][C:19]=2[CH2:20][C@H:21]1[O:22][CH3:23]Participants
Procedure
Acetyl chloride (278.8 mL, 3920 mmol) was added dropwise to ethanol (382 mL, 6530 mmol) at −5° C. over 2 h keeping the internal temperature below 20° C. The resulting solution was added portion wise over 15 min, keeping the internal temperature below 30° C., to a slurry of trans-(7-carbamoyl-1,1-diethyl-3-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (123.0 g, 327 mmol) and ethanol (500 mL) that had been cooled to 10° C. The reaction mixture was stirred at room temperature for 2 h, and concentrated to ˜200 mL by rotary evaporation. Ethyl acetate (200 mL) was added and the resulting slurry was stirred at 0° C. for 30 min, filtered and dried to yield the hydrochloride salt of the title compound (102 g, >98% purity) as a white solid.
Workup
- customthe internal temperature below 20° C
- additionThe resulting solution was added portion wise over 15 min
- customthe internal temperature below 30° C.
- concentrationconcentrated to ˜200 mL by rotary evaporation
- additionEthyl acetate (200 mL) was added
- stirringthe resulting slurry was stirred at 0° C. for 30 min
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-827d319503c6467c81168c76fb6777ff
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952031B2
Reaction notes
Loading…