Acetic Acid → allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 382631Notes

Reaction equation

HRID 382631 reaction equation
[Si]([O:8][C@@H:9]([C@H:11]1[C:32](=[O:33])[N:13]2[C:14]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[C:15]([C:18]3[N:25]4[C:21]([S:22][CH:23]=[CH:24]4)=[CH:20][N: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.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:32](=[O:33])[N:13]2[C:14]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[C:15]([C:18]3[N:25]4[C:21]([S:22][CH:23]=[CH:24]4)=[CH:20][N:19]=3)[C@H:16]([CH3:17])[C@H:12]12)[CH3:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131722905HCID 131722905, compound

Product 1

HCID 131722906allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylateYield 59.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.35 g of allyl (1S,5R,6S)-6-((1R)-1-t-butyldimethylsilyloxyethyl)-2-(imidazo[5,1-b]thiazole-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 12 ml of THF was added under ice-cooling 0.66 ml of acetic acid and 2.9 ml of a 1 M solution of tetra-n-butyl-ammonium fluoride in THF, and the mixture was stirred at room temperature for 36 hours. The reaction mixture was diluted with 50 ml of ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous saline in this sequence, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue thus obtained was purified by column chromatography on silica gel (ethyl acetate) to give 0.16 g of allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate and saturated aqueous saline in this sequence
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-fc931576017b4d49bbefb64a1bfd7770
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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