Acetic Acid → HCID 70150500, compound

HRID 382629Notes

Reaction equation

HRID 382629 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:17]2[C:13]([S:14][C:15]([C:18]3[C@H:19]([CH3:42])[C@@H:20]4[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]4[C:22]=3[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])=[CH:16]2)=[CH:12][N:11]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:40][C@@H:38]([C@H:37]1[C:36](=[O:41])[N:21]2[C:22]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=3)=[O:24])=[C:18]([C:15]3[S:14][C:13]4=[CH:12][N:11]=[C:10]([CH2:9][OH:8])[N:17]4[CH:16]=3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131722904HCID 131722904, compound

Product 1

HCID 70150500HCID 70150500, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 799 mg of 4-nitrobenzyl (1S,5R,6S)-2-(5-t-butyldimethylsilyloxymethylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 20 ml of THF were added 1.1 ml of acetic acid and 6.5 ml of 1 M solution of tetra-n-butylammonium fluoride in THF under the atmosphere of argon, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and diluted with 100 ml of ethyl acetate, 100 ml of aqueous saline and a saturated aqueous sodium hydrogen carbonate solution to adjust pH to 7.8. The organic layer was separated, washed with aqueous saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 619 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(5-hydroxymethylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with 100 ml of ethyl acetate, 100 ml of aqueous saline
  3. customThe organic layer was separated
  4. washwashed with aqueous saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by column chromatography on Sephadex

Sources & evidence

ORD record
ord-b58b83cbc7ca441f87f693deb5b31b22
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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