Acetic Acid → HCID 131722925, compound

HRID 382647Notes

Reaction equation

HRID 382647 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]2[C:17]([C:18]3[CH2:19][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][S:15][C:14]=12)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>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:17]3[N:13]4[CH:12]=[N:11][C:10]([CH2:9][OH:8])=[C:14]4[S:15][CH:16]=3)[CH2:19][C@H:20]12)[CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 131722926HCID 131722926, compound

Product 1

HCID 131722925HCID 131722925, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 848.8 mg of 848.8 mg of 4-nitrobenzyl (5R,6S)-2-(7-t-butyldimethylsilyloxymethylimidazo[5,1-b]thiazol-3-yl)-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate in 20 ml of THF was added 1.22 ml of acetic acid and 7.1 ml of a 1 M solution of tetra-n-butylammonium fluoride in THF, and the mixture was stirred at room temperature for 2.5 hours. After neutralizing the mixture with a saturated aqueous sodium hydrogen carbonate solution, it was extracted two times with ethyl acetate, washed with semi-saturated aqueous saline, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (ethyl acetate:methanol=9:1) to give 324.3 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-hydroxymethylimidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionwas extracted two times with ethyl acetate
  2. washwashed with semi-saturated aqueous saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography on silica gel (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-be03e055273944bb97c5be2b234ccbd2
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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