Dimethylformamide → benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate

HRID 1995790Notes

Reaction equation

HRID 1995790 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:45](=[O:46])[N:13]3[C:14]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:15]([CH2:19][S:20][C:21]4[N:22]=[N:23][N:24]([CH2:26][C:27]#[CH:28])[N:25]=4)[CH2:16][S:17](=O)[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.P(Cl)(Cl)Cl>O>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:45](=[O:46])[N:13]3[C:14]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:15]([CH2:19][S:20][C:21]4[N:22]=[N:23][N:24]([CH2:26][C:27]#[CH:28])[N:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 88675827benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 88675700benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylateYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

A mixture of benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate-1-oxide (16.0 g) and dry N,N-dimethylformamide (160 ml) was cooled to -30° C. and thereto was added phosphorus trichloride (6.7 g). The resulting solution was stirred for 50 minutes at -30° C. The reaction mixture was allowed to warm to ambient temperature, added to water (200 ml) and then extracted with ethyl acetate (x3). The extracts were combined, washed successively with a saturated aqueous solution of sodium bicarbonate (x3) and water (x3), dried over magnesium sulfate, treated with activated charcoal and then evaporated. The residue was pulverized in a mixture of isopropyl ether and n-hexane, collected by filtration, washed with n-hexane and then dried to give benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (14.33 g).

Workup

  1. temperatureto warm to ambient temperature
  2. extractionextracted with ethyl acetate (x3)
  3. washwashed successively with a saturated aqueous solution of sodium bicarbonate (x3) and water (x3)
  4. dry with materialdried over magnesium sulfate
  5. additiontreated with activated charcoal
  6. customevaporated
  7. additionThe residue was pulverized in a mixture of isopropyl ether and n-hexane
  8. filtrationcollected by filtration
  9. washwashed with n-hexane
  10. customdried

Sources & evidence

ORD record
ord-96b42b1058264c658c472c2462ae6e92
Source dataset
uspto-grants-1983_09
Patent number
US04405617

Reaction notes

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