Hydrogen chloride-ethyl acetate → HCID 86731257, compound
Reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:20]=[C:19]([O:21][CH2:22][C@@H:23]([NH:25]C(=O)OC(C)(C)C)[CH3:24])[CH:18]=[C:17]([F:33])[C:15]=4[N:16]=3)=[CH:8][C:7]=2[F:34])[CH2:3][CH2:2]1.Cl.[C:36](OCC)(=[O:38])[CH3:37]>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:20]=[C:19]([O:21][CH2:22][C@@H:23]([NH:25][C:36](=[O:38])[CH3:37])[CH3:24])[CH:18]=[C:17]([F:33])[C:15]=4[N:16]=3)=[CH:8][C:7]=2[F:34])[CH2:3][CH2:2]1Participants
Procedure
To tert-butyl ((2S)-1-((2-(4-(cyclopropylmethoxy)-3-fluorophenyl)-4-fluoro-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate (159 mg) was added 4 M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 10 min, and concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate/methanol, and the solution was subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated, and the obtained solid was recrystallized (hexane/ethyl acetate) to give the title compound as white crystals (73.5 mg).
Workup
- concentrationconcentrated
- additionTo the residue were added pyridine (10 mL) and acetic anhydride (10 mL)
- stirringthe mixture was stirred at room temperature for 15 min
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate/methanol
- customThe solvent was evaporated
- customthe obtained solid was recrystallized (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-fcb0c6fe8d234866ba7336d3f6ecbfd5
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133129B2
Reaction notes
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