Hydrochloric Acid → HCID 66874038, compound

HRID 249929Notes

Reaction equation

HRID 249929 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+:21].C([O-])(O)=O.[Na+].[CH:27]([O:30][C:31](Cl)=[O:32])([CH3:29])[CH3:28].Cl>C(Cl)(Cl)Cl.O>[CH:27]([O:30][C:31]([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]([O-:20])=[O:19])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)[C@@H:2]([CH3:1])[CH2:7]1)=[O:32])([CH3:29])[CH3:28].[Li+:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7917Isopropyl chloroformateHCID 516892Sodium BicarbonateHCID 66874398HCID 66874398, compound

Product 1

HCID 66874038HCID 66874038, 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 (208 mg, 0.743 mmol) and NaHCO3 (187 mg, 2.23 mmol) in chloroform (12 mL) and H2O (2 mL) was added dropwise isopropylchloroformate (1M solution in toluene, 892 mL, 0.891 mmol). The reaction mixture was stirred at room temperature for 2 h, then neutralized with 1N aqueous HCl. The mixture was concentrated under reduced pressure to provide lithium 2-((2S,6S)-4-(isopropoxycarbonyl)-2,6-dimethylpiperazin-1-yl)benzoxazole-4-carboxylate. MS consistent.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49074823afe3424583a7fba2fedce47c
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

Loading…