Methanol → Hydrochloric Acid

HRID 467376Notes

Reaction equation

HRID 467376 reaction equation
[O:1]=[C:2]1[CH:6]([S:7][C:8]2[CH2:9][S:10][C@@H:11]3[C@H:31]([NH:32]C(=O)CC4C=CC=CC=4)[C:30](=[O:42])[N:12]3[C:13]=2[C:14]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:5][CH2:4][O:3]1.CN1CCOCC1.P(Cl)(Cl)(Cl)(Cl)[Cl:51].CO>ClCCl.O>[NH2:32][C@@H:31]1[C:30](=[O:42])[N:12]2[C:13]([C:14]([O:16][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:15])=[C:8]([S:7][CH:6]3[CH2:5][CH2:4][O:3][C:2]3=[O:1])[CH2:9][S:10][C@H:11]12.[ClH:51]

Participants

8

Reactant 4

HCID 887MethanolHCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 67908892HCID 67908892, compound

Product 2

HCID 313Hydrochloric AcidHCID 67908800HCID 67908800, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Diphenylmethyl 3-(2-oxotetrahydrofuran-3-ylthio)-7β-phenylacetamidoceph-3-em-4-carboxylate (733 mg) was suspended in dry dichloromethane (10 ml) under an inert atmosphere. The reaction was cooled to -20° C. and treated with N-methylmorpholine (269 μl) followed by a solution of phosphorus pentachloride in dichloromethane (9.5 ml of 40 mgml-1 solution). The now homogeneous solution was stirred at -20° C. for 30 min. Treated with methanol (2.44 ml) and then continued stirring whilst allowing to warm to room temperature. After 30 min. water (3.3 ml) was added and the solution vigorously stirred for a final 30 min. The organic solvent was removed by evaporation in vacuo. The resulting solid was removed from the aqueous phase by filtration and was washed with water and then ether. Drying the solid over phosphorus pentoxide in vacuo gave the crude title compound in the form of its hydrochloride (621 mg). (c) Diphenylmethyl 3-(2-Oxotetrahydrofuran-3-ylthio)-7β-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]ceph-3-em-4-carboxylate.

Workup

  1. stirringcontinued stirring
  2. temperatureto warm to room temperature
  3. stirringthe solution vigorously stirred for a final 30 min
  4. customThe organic solvent was removed by evaporation in vacuo
  5. customThe resulting solid was removed from the aqueous phase by filtration
  6. washwas washed with water
  7. dry with materialDrying the solid over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-1f8a9e5222a74f599bc6de796b6b3128
Source dataset
uspto-grants-1992_10
Patent number
US05158946

Reaction notes

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