Methane → HCID 131711554, compound

HRID 971502Notes

Reaction equation

HRID 971502 reaction equation
[O:1]([C:8]([CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](Cl)=[O:12])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][CH:21]1[C:39](=[O:40])[N:23]2[C:24]([C:36]([OH:38])=[O:37])=[C:25]([CH2:28][S:29][C:30]3[N:34]([CH3:35])[N:33]=[N:32][N:31]=3)[CH2:26][S:27][C@H:22]12.C(N(CC)CC)C.C>ClCCl.C(=O)(O)[O-].[Na+]>[O:1]([C:8]([CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([NH:20][CH:21]1[C:39](=[O:40])[N:23]2[C:24]([C:36]([OH:38])=[O:37])=[C:25]([CH2:28][S:29][C:30]3[N:34]([CH3:35])[N:33]=[N:32][N:31]=3)[CH2:26][S:27][C@H:22]12)=[O:12])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 12771215Phenyl 3-chloro-3-oxo-2-phenylpropanoateHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

Product 1

HCID 131711554HCID 131711554, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

α-(Phenoxycarbonyl)phenylacetyl chloride (0.02 M) in dichloromethane (50 ml.) was added to 7-amino-3-(1-methyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid (6.56 g., 0.02 M) and triethylamine (6.0 ml.) in dichloromethane (100 ml.). The resulting solution was stirred at room temperature for three hours then the solvent was removed in vacuo, the residue dissolved in water (200 ml.) and washed with ethyl acetate (2×100 ml.). The aqueous solution was covered with ethyl acetate (50 ml.) acidified to pH 1.5 with 1 N hydrochloric acid, filtered, the organic phase was collected and the aqueous phase extracted with more ethyl acetate (50 ml.). The combined extracts were washed with water (2×100 ml.) and saturated sodium chloride (50 ml.) dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo to give an oily residue which was triturated with anhydrous ether to give a pale brown solid (5.0 g.). This solid was dissolved in dilute sodium bicarbonate solution (100 ml.), treated with decolourising charcoal, filtered, acidified to pH 1.5 and the precipitated cephalosporin free acid collected and dried in vacuo.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (200 ml.)
  3. washwashed with ethyl acetate (2×100 ml.)
  4. filtrationfiltered
  5. customthe organic phase was collected
  6. extractionthe aqueous phase extracted with more ethyl acetate (50 ml.)
  7. washThe combined extracts were washed with water (2×100 ml.) and saturated sodium chloride (50 ml.)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated to dryness in vacuo
  10. customto give an oily residue which
  11. customwas triturated with anhydrous ether
  12. customto give a pale brown solid (5.0 g.)
  13. filtrationfiltered
  14. customthe precipitated cephalosporin free acid collected
  15. customdried in vacuo

Sources & evidence

ORD record
ord-d130598cba44427db91664eb6322313a
Source dataset
uspto-grants-1979_07
Patent number
US04160086

Reaction notes

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