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

HRID 1284652Notes

Reaction equation

HRID 1284652 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.C1(CC([NH:22][CH:23]2[C:56](=[O:57])[N:25]3[C:26]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[C:27]([CH2:30][S:31][C:32]4[N:33]=[N:34][N:35]([CH2:37][C:38]#[CH:39])[N:36]=4)[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.CO>C(Cl)Cl>[NH2:22][CH:23]1[C:56](=[O:57])[N:25]2[C:26]([C:40]([O:42][CH:43]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[O:41])=[C:27]([CH2:30][S:31][C:32]3[N:33]=[N:34][N:35]([CH2:37][C:38]#[CH:39])[N:36]=3)[CH2:28][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 88675700benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate

Product 1

HCID 88675652benzhydryl 7-amino-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of phosphorus pentachloride (8.5 g) in methylene chloride (130 ml) was cooled to 5° C. and thereto was added pyridine (3.2 g). The mixture was stirred for 30 minutes at room temperature, cooled to 5° C. and thereto was added benzhydryl 7-(2-phenylacetamido)-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (13.0 g) to give a homogeneous solution. The obtained solution was stirred for 30 minutes at 5° C. and added to methanol (65.4 g) precooled to -30° C. The resulting mixture was stirred for 30 minutes without external cooling. The reaction mixture was evaporated and to the residue were added ethyl acetate and water. The mixture was adjusted to pH 7.0 with a saturated aqueous solution of sodium carbonate. The ethyl acetate layer was separated, washed with water (×3), dried over magnesium sulfate, treated with activated charcoal and evaporated under reduced pressure to give benzhydryl 7-amino-3-[2-(2-propynyl)-2H-tetrazol-5- yl]thiomethyl-3-cephem-4-carboxylate (7.31 g).

Workup

  1. temperaturecooled to 5° C.
  2. customto give a homogeneous solution
  3. stirringThe obtained solution was stirred for 30 minutes at 5° C.
  4. customprecooled to -30° C
  5. stirringThe resulting mixture was stirred for 30 minutes without external cooling
  6. customThe reaction mixture was evaporated and to the residue
  7. additionwere added ethyl acetate and water
  8. customThe ethyl acetate layer was separated
  9. washwashed with water (×3)
  10. dry with materialdried over magnesium sulfate
  11. additiontreated with activated charcoal
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c7aafcd03bc04a86a4d2b91d7860a468
Source dataset
uspto-grants-1986_01
Patent number
US04563450

Reaction notes

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