Acetone → HCID 178429814, compound

HRID 2358937Notes

Reaction equation

HRID 2358937 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[CH3:13][C@@:14]1([CH2:27][N:28]2[N:32]=[N:31][CH:30]=[CH:29]2)[S:18](=[O:20])(=[O:19])[C@@H:17]2[CH2:21][C:22](=[O:23])[N:16]2[C@H:15]1[C:24]([OH:26])=[O:25].CC(C)=O>O.CC(C)=O>[CH3:13][C@@:14]1([CH2:27][N:28]2[N:32]=[N:31][CH:30]=[CH:29]2)[S:18](=[O:19])(=[O:20])[C@@H:17]2[CH2:21][C:22](=[O:23])[N:16]2[C@H:15]1[C:24]([OH:26])=[O:25].[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 123630TazobactamHCID 178418600HCID 178418600, compound

Product 1

HCID 178429814HCID 178429814, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
30 °C

Procedure

L-arginine (1.16 g) was charged to the reactor and dissolved in a mixture of deionized water-acetone (1:1, v/v, 40 mL) by mechanically stirring at 300 rpm, 30° C. over 5 min. Tazobactam acid (2.00 g) was then added to the above solution over 2 min with the observed pH change from 10.5±0.5 to 5.9±0.5. After adding 34.5 mL of acetone over 30 min at 30° C., crystallization started, then the suspension was cooled down to 15° C. at 0.1° C./min and kept stirring at 15° C. for additional 1.5 hr. White fine needle crystals were filtered out and vacuum dried for 2 hours at 35° C. to obtain 2.59 g (82% yield) of tazobactam arginine polymorph Ia.

Workup

  1. customcrystallization
  2. temperaturethe suspension was cooled down to 15° C. at 0.1° C./min
  3. stirringkept stirring at 15° C. for additional 1.5 hr
  4. filtrationWhite fine needle crystals were filtered out
  5. customvacuum dried for 2 hours at 35° C.

Sources & evidence

ORD record
ord-155e6fe35f1a4099833c8833d4aa7314
Source dataset
uspto-grants-2014_04
Patent number
US08685957B1

Reaction notes

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