Phenol → HCID 178431933, compound

HRID 614159Notes

Reaction equation

HRID 614159 reaction equation
[C:1]1([C:7]([C:10](Cl)=[O:11])=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:20][CH:21]1[C:34](=[O:35])[N:23]2[CH:24]([C:29]3[NH:33][N:32]=[N:31][N:30]=3)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]12>C(Cl)(Cl)Cl.C(N(CC)CC)C>[O:19]([C:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:10]([NH:20][CH:21]1[C:34](=[O:35])[N:23]2[CH:24]([C:29]3[NH:30][N:31]=[N:32][N:33]=3)[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]12)=[O:11])=[O:9])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 107737343-Oxo-2-phenylprop-2-enoyl chlorideHCID 178431949HCID 178431949, compound

Product 1

HCID 178431933HCID 178431933, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

A stirred solution of 1.80 g. of phenyl chlorocarbonyl ketene (U.S. Pat. No. 3,679,801) in 20 ml. of chloroform is cooled to -40° C., and then 0.94 g of phenol is added. Stirring is continued at -40° C. for a further 20 minutes, and then a solution of 2.40 g. of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam and 1.40 ml of triethylamine in 50 ml. of chloroform is added dropwise. The cooling bath is removed, and the mixture stirred for a further 30 minutes. The mixture is filtered, and the chloroform is evaporated in vacuo to give crude 6-(2-phenoxycarbonyl-2-phenylacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam, as its triethylamine salt.

Workup

  1. customThe cooling bath is removed
  2. stirringthe mixture stirred for a further 30 minutes
  3. filtrationThe mixture is filtered
  4. customthe chloroform is evaporated in vacuo

Sources & evidence

ORD record
ord-d8097e709cdf42abbc4b241dbdd932f4
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

Loading…