Acetic Acid → HCID 70150416, compound

HRID 382637Notes

Reaction equation

HRID 382637 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]2[CH:17]=[C:16]([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])[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:16]3[S:15][C:14]4=[C:10]([CH2:9][OH:8])[N:11]=[CH:12][N:13]4[CH:17]=3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 131722908HCID 131722908, compound

Product 1

HCID 70150416HCID 70150416, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 334.6 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-t-butyldimethylsilyloxymethylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 10 ml of THF were added 0.28 ml of acetic acid and 1.64 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 the reaction mixture was adjusted to pH 8.2 with a saturated aqueous sodium hydrogen carbonate solution, it was extracted twice with ethyl acetate, and semi-saturated aqueous saline. The organic layer was 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 183 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-hydroxylmethylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionwas extracted twice with ethyl acetate, and semi-saturated aqueous saline
  2. dry with materialThe organic layer was dried 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:methanol=9:1)

Sources & evidence

ORD record
ord-f0b8ae55cc5140edbb1a450fbc054a2b
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

Loading…