Phenylacetyl chloride → HCID 70582920, compound

HRID 2052175Notes

Reaction equation

HRID 2052175 reaction equation
[NH2:1][CH:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([C:9]3[S:10][C:11]([N:14]([CH3:16])[CH3:15])=[N:12][N:13]=3)[CH2:7][S:8][C@H:3]12.[C:35]1([CH2:41][C:42](Cl)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C>ClCCl>[C:35]1([CH2:41][C:42]([NH:1][CH:2]2[C:33](=[O:34])[N:4]3[C:5]([C:17]([O:19][CH:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])=[C:6]([C:9]4[S:10][C:11]([N:14]([CH3:16])[CH3:15])=[N:12][N:13]=4)[CH2:7][S:8][C@H:3]23)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 70582709HCID 70582709, compound

Product 1

HCID 70582920HCID 70582920, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.491 g of benzhydryl 7-amino-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate (obtained in Example 26) in 16 ml of dichloromethane is dropwise added 0.160 g of phenylacetylchloride and 0.10 g of triethylamine with stirring under ice-cooling, and stirring and cooling are maintained for 30 minutes. The reaction mixture is washed with water, dried over anhydrous sodium sulfate and the solvent is removed in vacuo. The residue is chromatographed on a column of silica gel [eluted with benzene-ethyl acetate(1:3)] to give 0.51 g of benzhydryl 7-phenylacetamido-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate.

Workup

  1. temperaturecooling
  2. stirringstirring
  3. temperaturecooling
  4. temperatureare maintained for 30 minutes
  5. washThe reaction mixture is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent is removed in vacuo
  8. customThe residue is chromatographed on a column of silica gel [eluted with benzene-ethyl acetate(1:3)]

Sources & evidence

ORD record
ord-c1c8037dc5eb48fc85d5d0bb4528e749
Source dataset
uspto-grants-1980_01
Patent number
US04182866

Reaction notes

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