Hydrochloric Acid → HCID 131714961, compound

HRID 1731697Notes

Reaction equation

HRID 1731697 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:48][O:49][CH2:50][CH:51]=[CH2:52])[C:10]([NH:12][CH:13]2[C:46](=[O:47])[N:15]3[C:16]([C:30]([O:32][CH:33]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])=[C:17]([CH2:20][S:21]/[CH:22]=[CH:23]\[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.O1CCCC1.O>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:48][O:49][CH2:50][CH:51]=[CH2:52])[C:10]([NH:12][CH:13]2[C:46](=[O:47])[N:15]3[C:16]([C:30]([O:32][CH:33]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])=[C:17]([CH2:20][S:21]/[CH:22]=[CH:23]\[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131714962HCID 131714962, compound

Product 1

HCID 131714961HCID 131714961, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (23.5 g) in methanol (950 ml) was added conc. hydrochloric acid (12.7 ml) at ambient temperature. The mixture was stirred for 50 minutes at 35° C. The mixture was concentrated in vacuo to give a residue, which was dissolved in a mixture of ethyl acetate, tetrahydrofuran and water. The mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated in vacuo, and the residue was triturated in diisopropyl ether to give benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (21.5 g)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue, which
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-b6f3ec10a28a4f19a157deea9c2a7673
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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