Acetic Acid → HCID 57643907, compound

HRID 2113299Notes

Reaction equation

HRID 2113299 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:30][C@@H:31]([C@H:33]1[C:62](=[O:63])[N:35]2[C:36]([C:56]([O:58][CH2:59][CH:60]=[CH2:61])=[O:57])=[C:37]([C:40]3[S:44][C:43]4=[C:45]([C:48]([C:50]5[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=5)=[O:49])[N:46]=[CH:47][N:42]4[CH:41]=3)[C@H:38]([CH3:39])[C@H:34]12)[CH3:32])(C(C)(C)C)(C)C>O1CCCC1.C(OCC)(=O)C>[OH:30][C@@H:31]([C@H:33]1[C:62](=[O:63])[N:35]2[C:36]([C:56]([O:58][CH2:59][CH:60]=[CH2:61])=[O:57])=[C:37]([C:40]3[S:44][C:43]4=[C:45]([C:48]([C:50]5[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=5)=[O:49])[N:46]=[CH:47][N:42]4[CH:41]=3)[C@H:38]([CH3:39])[C@H:34]12)[CH3:32]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 57643895HCID 57643895, compound

Product 1

HCID 57643907HCID 57643907, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.23 ml) and 0.72 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added to a solution of 0.14 g of allyl (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate in 2 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 36 hr. The reaction mixture was diluted with 50 ml of ethyl acetate, and the diluted reaction solution was washed with a 50% aqueous sodium bicarbonate solution and 10% brine in that order. The organic layer was dried, and the solvent was then removed by evaporation. The resultant crude product was purified by column chromatography on silica gel (eluted with 10% methanol/ethyl acetate) to give 60.3 mg of allyl (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate. This product was analyzed by NMR. The results were in agreement with the results of analysis in Example 26.

Workup

  1. customthe diluted reaction solution
  2. washwas washed with a 50% aqueous sodium bicarbonate solution and 10% brine in that order
  3. customThe organic layer was dried
  4. customthe solvent was then removed by evaporation
  5. customThe resultant crude product was purified by column chromatography on silica gel (eluted with 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-87db563ed71c4189a2a76920cfbe3b23
Source dataset
uspto-grants-2009_04
Patent number
US07524951B2

Reaction notes

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