HCID 70505024, compound → HCID 70504783, compound

HRID 1463144Notes

Reaction equation

HRID 1463144 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:14]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:15]([CH3:17])[S:16][C@H:11]12)=[O:8]>C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([OH:25])=[O:24])=[C:14]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:15]([CH3:17])[S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 1

HCID 70505024HCID 70505024, compound

Product 1

HCID 70504783HCID 70504783, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 1.4 g of diphenylmethyl 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate in 3 ml of anisole and 20 ml of CF3COOH was stirred at room temperature for 15 minutes. After distilling off CF3COOH under reduced pressure, the residue was dissolved in AcOEt, and then transferred into 5% aqueous NaHCO3. The water layer was adjusted to pH 2.0 with 5% H3PO4 to extract again with AcOEt. The AcOEt layer was washed with saturated aqueous NaCl solution, and dried over Na2SO4, and the AcOEt was distilled off under reduced pressure, thus yielding crude crystals of 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylic acid. The crude crystals were dissolved in 5% aqueous NaHCO3, adjusted to pH 7.0 with addition of 5% H3PO4 and then added on a column of Amberlite XAD-II (produced by Rohm & Hass). The fractions eluted with H2O were collected, concentrated under reduced pressure and freeze-dried, thus yielding 829 mg (79%) of sodium 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate.

Workup

  1. distillationAfter distilling off CF3COOH under reduced pressure
  2. dissolutionthe residue was dissolved in AcOEt
  3. extractionto extract again with AcOEt
  4. washThe AcOEt layer was washed with saturated aqueous NaCl solution
  5. dry with materialdried over Na2SO4
  6. distillationthe AcOEt was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f7861f2b0372479caef43171e563ec1d
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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