Acetic Acid → HCID 12069976, compound

HRID 382608Notes

Reaction equation

HRID 382608 reaction equation
[Si]([O:8][C@@H:9]([C@H:11]1[C:39](=[O:40])[N:13]2[C:14]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:15]([C:18]3[S:22][C:21]4=[CH:23][N:24]=[CH:25][N:20]4[CH:19]=3)[C@H:16]([CH3:17])[C@H:12]12)[CH3:10])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C1COCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:39](=[O:40])[N:13]2[C:14]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:27])=[C:15]([C:18]3[S:22][C:21]4=[CH:23][N:24]=[CH:25][N:20]4[CH:19]=3)[C@H:16]([CH3:17])[C@H:12]12)[CH3:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11078149TBAF tetrahydrofuranHCID 131722900HCID 131722900, compound

Product 1

HCID 12069976HCID 12069976, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 111 mg of 4-nitrobenzyl (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 3 ml of anhydrous THF were added 0.164 ml of acetic acid and 0.954 ml of a 1 M solution of tetra-n-butylammonium fluoride/THF, and the mixture was stirred at room temperature under the atmosphere of argon at 20 hours. The reaction mixture was diluted with ethyl acetate, and washed with a mixed solvent of semi-saturated aqueous saline and saturated aqueous sodium hydrogen carbonate (pH 8.0), and semi-saturated aqueous saline in this sequence. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation. The residue thus obtained was purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 57.3 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. washwashed with a mixed solvent of semi-saturated aqueous saline and saturated aqueous sodium hydrogen carbonate (pH 8.0), and semi-saturated aqueous saline in this sequence
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by distillation
  5. customThe residue thus obtained
  6. customwas purified by column chromatography on Sephadex

Sources & evidence

ORD record
ord-1a83766d3fd24791a88640f14f9ca684
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

Loading…