Methanol → HCID 88675660, compound

HRID 1284651Notes

Reaction equation

HRID 1284651 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:36]([CH2:37][C:38]#[CH:39])[N:35]=[N:34][N:33]=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:36]([CH2:37][C:38]#[CH:39])[N:35]=[N:34][N:33]=3)[CH2:28][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 88675687HCID 88675687, compound

Product 1

HCID 88675660HCID 88675660, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of phosphorus pentachloride (5.3 g) in methylene chloride (80 ml) was cooled to 5° C. and thereto was added pyridine (2.0 g). The mixture was stirred for 30 minutes at room temperature and then cooled to 5° C. and thereto was added benzhydryl 7-(2-phenylacetamido)-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (8.0 g) to give a homogeneous solution. The obtained solution was stirred for 30 minutes at 5° C. and added to methanol (40.2 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 pressine to give benzhydryl 7-amino-3 -[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (6.17 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 pressine

Sources & evidence

ORD record
ord-b210e7b517cb4b9db45f9d2151afdb3d
Source dataset
uspto-grants-1986_01
Patent number
US04563450

Reaction notes

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