Hydrochloric Acid → HCID 11589807, compound
Reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C@H:11]([C:13](=[O:18])N(OC)C)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:34])([F:33])[C:22]1[CH:23]=[C:24](Br)[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.C([Mg]Cl)(C)C.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C@@H:11]([CH3:12])[C:13]([C:24]1[CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=[C:22]([C:21]([F:20])([F:34])[F:33])[CH:23]=1)=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
[(S)-1-(Methoxy-methyl-carbamoyl)-ethyl]-carbamic acid benzyl ester (5 g, 18.8 mmol) and 3,5-bis(trifluoromethyl)bromobenzene (4.04 mL, 23.5 mmol) were dissolved in THF (20 mL). The solution was degassed with N2 for 5 minutes, and then cooled to 0° C. Isopropylmagnesium chloride (2M in THF; 23.5 mL, 46.9 mmol) was added slowly, and the reaction was stirred at room temperature for 2 hours. Once no starting material was seen by analytical tlc, the mixture was cooled to 0° C. 1N Aqueous HCl (55 mL) was added, and the organic layer was separated and washed with brine. After concentrating, the crude material was purified by silica gel chromatography to give the title compound.
Workup
- customThe solution was degassed with N2 for 5 minutes
- temperaturethe mixture was cooled to 0° C
- customthe organic layer was separated
- washwashed with brine
- concentrationAfter concentrating
- customthe crude material was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-635721063ce64bc9aab5fc754ef31d58
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497381B2
Reaction notes
Loading…