Sodium hydride → HCID 66875077, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH:14]([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:20]1[O:21][C:22]2[C:23](=[C:25]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][CH:28]=2)[N:24]=1>COCCOC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:20]2[O:21][C:22]3[C:23](=[C:25]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][CH:28]=3)[N:24]=2)[CH2:10][C@@H:9]1[CH:14]([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a solution of 1-tert-butyloxycarbonyl-(S)-2-isopropylpiperazine (384 mg, 1.7 mmol) in DME (10 mL) was added NaH (70 mg of 60% suspension in mineral oil, 1.6 mmol) and the mixture was stirred for 1 h at room temperature. Methyl 2-chlorobenzoxazole-4-carboxylate (368 mg, 1.6 mmol) was added to the reaction mixture and suspension formed was stirred at room temperature for 17 h. The reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL) was added, and solvent removed under reduced pressure. The mixture was purified by column chromatography (silica gel, 0 to 80% EtOAc in CH2Cl2) to afford methyl 2-(4-(tert-butoxycarbonyl)-(S)-3-isopropylpiperazin-1-yl)benzoxazole-4-carboxylate (255 mg, 39%) as a white foam. 1H NMR and MS consistent.
Workup
- customformed
- stirringwas stirred at room temperature for 17 h
- customThe reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL)
- additionwas added
- customsolvent removed under reduced pressure
- customThe mixture was purified by column chromatography (silica gel, 0 to 80% EtOAc in CH2Cl2)
Sources & evidence
- ORD record
- ord-e102442a334a438fb9cd71d3ac56dd82
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863271B2
Reaction notes
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