Phosphorus trichloride → Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate

HRID 596836Notes

Reaction equation

HRID 596836 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:40](=[O:41])[N:12]2[C:13]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:14]([CH:18]([O:20][C:21](=[O:23])[CH3:22])[CH3:19])[CH2:15][S:16](=O)[C@H:11]12)=[O:8].P(Cl)(Cl)Cl>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:40](=[O:41])[N:12]2[C:13]([C:24]([O:26][CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:25])=[C:14]([CH:18]([O:20][C:21](=[O:23])[CH3:22])[CH3:19])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 70617865Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 70617769Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of 0.514 g. of benzhydryl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide (isomer II from the previous example) in 15 ml. of dimethylformamide was added 0.190 ml. of phosphorous trichloride. The reaction mixture was removed from the ice-bath and allowed to warm to room temperature at which temperature it was stirred for one hour. The reaction mixture was then transferred with the aid of ethyl acetate to a separatory funnel and was then washed with aqueous sodium bicarbonate solution (2X), and brine (2X) and then dried over anhydrous sodium sulfate. Evaporation in vacuo provided a product which was chromatographed on a silica gel column using a toluene-ethyl acetate gradient to give 0.328 g. (65.5 percent) of the title product as a froth:

Workup

  1. customThe reaction mixture was removed from the ice-bath
  2. customThe reaction mixture was then transferred with the aid of ethyl acetate to a separatory funnel
  3. washwas then washed with aqueous sodium bicarbonate solution (2X), and brine (2X)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation in vacuo
  6. customprovided a product which
  7. customwas chromatographed on a silica gel column
  8. customto give 0.328 g

Sources & evidence

ORD record
ord-531a62fbce0e439c9635f04fe81e26c6
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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