Sodium hydride → methyl 2-(4-(tert-butoxycarbonyl)-(3S)-3-isobutylpiperazine-1-yl)benzoxazole-4-carboxylate

HRID 249864Notes

Reaction equation

HRID 249864 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:21]1[O:22][C:23]2[C:24](=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:28][CH:29]=2)[N:25]=1>COCCOC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21]2[O:22][C:23]3[C:24](=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:28][CH:29]=3)[N:25]=2)[CH2:10][C@@H:9]1[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 17750437tert-Butyl (2S)-2-(2-methylpropyl)piperazine-1-carboxylateHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66874322methyl 2-(4-(tert-butoxycarbonyl)-(3S)-3-isobutylpiperazine-1-yl)benzoxazole-4-carboxylateYield 32.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-(2S)-2-isobutylpiperazine (384 mg, 1.6 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)-(3S)-3-isobutylpiperazine-1-yl)benzoxazole-4-carboxylate (219 mg, 32%) as a clear oil: 1H NMR and MS consistent.

Workup

  1. customformed
  2. stirringwas stirred at room temperature for 17 h
  3. customThe reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL)
  4. additionwas added
  5. customsolvent removed under reduced pressure
  6. customThe mixture was purified by column chromatography ((silica gel, 0 to 80% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-545bf96c17254a04a21bf082b1d8fb58
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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