Acetic Acid → HCID 70504358, compound

HRID 1463141Notes

Reaction equation

HRID 1463141 reaction equation
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]([NH:11][CH:12]1[C:41](=[O:42])[N:14]2[C:15]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[C:16]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:17](=[CH2:19])[S:18][C@H:13]12)=[O:10].CC(O)=O>CCO.O1CCCC1>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]([NH:11][CH:12]1[C:41](=[O:42])[N:14]2[CH:15]([C:25]([O:27][CH:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:26])[C:16]([CH2:20][O:21][C:22](=[O:24])[CH3:23])=[C:17]([CH3:19])[S:18][C@H:13]12)=[O:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 70504655HCID 70504655, compound

Product 1

HCID 70504358HCID 70504358, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.4 g of NaBH4 in 250 ml of EtOH was added to a solution of 45 g of diphenylmethyl 7-(2-thienylacetamido)-2-methylene-3-acetoxymethylceph-3-em-4-carboxylate in 150 ml of tetrahydrofuran at 0° C., and the mixture was stirred for 7 minutes, followed by adding 15 ml of AcOH. After distilling off the solvent under reduced pressure, AcOEt and H2O were added to the residue to separate out the AcOEt layer. The AcOEt layer was washed with 5% aqueous NaHCO3 and saturated aqueous sodium chloride solution, and dried over Na2SO4 to distill off the AcOEt under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.AcOEt (10:1) were collected, followed by distilling off the solvent under reduced pressure, yielding 18.7 g (41%) of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-acetoxymethylceph-2-em-4-carboxylate.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure, AcOEt and H2O
  2. additionwere added to the residue
  3. customto separate out the AcOEt layer
  4. washThe AcOEt layer was washed with 5% aqueous NaHCO3 and saturated aqueous sodium chloride solution
  5. dry with materialdried over Na2SO4
  6. distillationto distill off the AcOEt under reduced pressure
  7. additionThe residue was added on a column of silica gel
  8. washthe fractions eluted with CH2Cl2
  9. customAcOEt (10:1) were collected
  10. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-634c13f2bebc407395c4139fbe3dd371
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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