Acetic Acid → HCID 131715979, compound

HRID 1905101Notes

Reaction equation

HRID 1905101 reaction equation
C(O)(=[O:3])C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:23]1[CH:28]=[CH:27][C:26]([S:29][C:30]2[CH2:31][C@@H:32]3[C@H:42]([C@H:43]([C:49](C)(C)C)CO[SiH](C)C)[C:41](=[O:53])[N:33]3[C:34]=2[C:35]([O:37][CH2:38][CH:39]=[CH2:40])=[O:36])=[CH:25][CH:24]=1>C1COCC1>[N:23]1[CH:28]=[CH:27][C:26]([S:29][C:30]2[CH2:31][C@@H:32]3[C@@H:42]([C@H:43]([OH:3])[CH3:49])[C:41](=[O:53])[N:33]3[C:34]=2[C:35]([O:37][CH2:38][CH:39]=[CH2:40])=[O:36])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131715978HCID 131715978, compound

Product 1

HCID 131715979HCID 131715979, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.69 ml (64.5 mmol - 10 equivalents) of glacial acetic acid and 19.3 ml (19.3 mmol - 3 equivalents) of a 1M solution of tetrabutylammonium fluoride in THF were added to a solution, which had been cooled to 0° C., of 2.97 g (6.5 mmol) of allyl (5R,6S)-2-(4-pyridylthio)-6-[(1R)-1-tert.-butyldimethylsilyloxyethyl]carbapen-2-em-3-carboxylate in 60 ml of THF. The cooling bath was removed and the reaction solution was allowed to stand at room temperature for 62 h. To work up, it was poured a into a mixture of cold, saturated NaHCO3 solution and ethyl acetate, extraction with ethyl acetate was carried out, followed by washing with saturated NaHCO3 and NaCl solutions and drying over MgSO4. After evaporation of the solvent in vacuo and chromatography of the residue on 360 g of silica gel (toluene:ethyl acetate 9:1), 472 mg (21%) of the title compound were obtained as an oil, Rf: 0.24 (toluene:ethyl acetate 9:1).

Workup

  1. customThe cooling bath was removed
  2. additionit was poured a
  3. additioninto a mixture of cold,
  4. extractionsaturated NaHCO3 solution and ethyl acetate, extraction with ethyl acetate
  5. washby washing with saturated NaHCO3 and NaCl solutions
  6. dry with materialdrying over MgSO4
  7. customAfter evaporation of the solvent in vacuo and chromatography of the residue on 360 g of silica gel (toluene:ethyl acetate 9:1)

Sources & evidence

ORD record
ord-0d4fbd915ec64433b3db7b61285d2532
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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