Hydrochloric Acid → HCID 66874448, compound

HRID 249925Notes

Reaction equation

HRID 249925 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@H:4]([CH3:8])[N:3]1[C:9]1[O:10][C:11]2[C:12](=[C:14]([C:18]([O-:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)[N:13]=1.[Li+].C([O-])(O)=O.[Na+].Cl[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29].Cl>C(Cl)(Cl)Cl.O>[CH2:31]([O:30][C:28]([N:6]1[CH2:5][C@H:4]([CH3:8])[N:3]([C:9]2[O:10][C:11]3[C:12](=[C:14]([C:18]([OH:20])=[O:19])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)[C@@H:2]([CH3:1])[CH2:7]1)=[O:29])[CH:32]([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 66874398HCID 66874398, compound

Product 1

HCID 66874448HCID 66874448, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a vigorously stirred suspension of lithium 2-((2S,6S)-2,6-dimethylpiperazin-1-yl)benzoxazole-4-carboxylate (97 mg, 0.346 mmol) and NaHCO3 (87 mg, 1.037 mmol) in chloroform (6 mL) and H2O (6 mL) was added dropwise isobutyl chloroformate (54 mL, 0.415 mmol). The reaction mixture was stirred at room temperature for 2 h, then neutralized with 1N aqueous HCl, and concentrated under reduced pressure to provide 2-((2S,6S)-4-(isobutoxycarbonyl)-2,6-dimethylpiperazin-1-yl)benzoxazole-4-carboxylic acid. MS consistent.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e13a6856a7134afcab918f39fe673455
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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