Methanol → HCID 11873141, compound

HRID 1833891Notes

Reaction equation

HRID 1833891 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].CO.C(OO)(=[O:28])C>C(Cl)Cl>[CH3:1][C:2]1[CH2:3][S@:4](=[O:28])[C@@H:5]2[C@H:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 6585Peracetic AcidHCID 168674Phenylacetyl 7-aminodesacetoxycephalosporanic acid

Product 1

HCID 11873141HCID 11873141, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of polymer ester of (6R, 7R)-3-methyl-7-phenylacetamidoceph-3-em-4-carboxylic acid (5.00g, 4.45 mole, from example 8 in methylene chloride (35 ml.) and methanol (10 ml.) cooled to 0° was added peracetic acid (38% w/v, 1.1 ml., 5.50 m.mole) in one portion. Stirring was continued for 30 minutes at 0° and for a further 15 minutes, after removal of the cooling bath. The reaction mixture was filtered and pulled as dry as possible. The product was washed with methylene chloride (2 × 50 ml.) methanol (2 × 50 ml.), and methylene chloride (2 × 50 ml.). The product was dried to constant weight in vacuo at 30° to give the pale yellow polymer ester of (1S, 6R. 7R)-3-methyl-7-phenylacetamidoceph-3-em-4-carboxylic acid 1-oxide (5.00g, which proved to be similar (infra red, nmr., and t.l.c.) with the product obtained in example 9 above.

Workup

  1. customafter removal of the cooling bath
  2. filtrationThe reaction mixture was filtered
  3. customas dry as possible
  4. washThe product was washed with methylene chloride (2 × 50 ml.) methanol (2 × 50 ml.), and methylene chloride (2 × 50 ml.)
  5. customThe product was dried to constant weight in vacuo at 30°

Sources & evidence

ORD record
ord-da61dae431ad4fb7a11a5559a0e6f1b4
Source dataset
uspto-grants-1978_01
Patent number
US04067858

Reaction notes

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