Hydrochloric Acid → HCID 131713200, compound

HRID 1195565Notes

Reaction equation

HRID 1195565 reaction equation
[C:1]([O:5][C:6](/[CH:8]=[CH:9]/[CH2:10][O:11][N:12]=[C:13]([C:44]1[N:45]=[C:46]([NH:49]C=O)[S:47][CH:48]=1)[C:14]([NH:16][CH:17]1[C:42](=[O:43])[N:19]2[C:20]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:21]([CH:24]=[CH2:25])[CH2:22][S:23][C@H:18]12)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)(O)[O-].[Na+].C(OC(C)C)(C)C>C(OCC)(=O)C.O1CCCC1.CO>[C:1]([O:5][C:6](/[CH:8]=[CH:9]/[CH2:10][O:11][N:12]=[C:13]([C:44]1[N:45]=[C:46]([NH2:49])[S:47][CH:48]=1)[C:14]([NH:16][CH:17]1[C:42](=[O:43])[N:19]2[C:20]([C:26]([O:28][CH:29]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:27])=[C:21]([CH:24]=[CH2:25])[CH2:22][S:23][C@H:18]12)=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 131713207HCID 131713207, compound

Product 1

HCID 131713200HCID 131713200, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzhydryl 7-[2-(trans-3-tert-butoxycarbonylallyloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (4.7 g), conc. hydrochloric acid (1.34 g), methanol (30 ml) and tetrahydrofuran (10 ml) was stirred at ambient temperature for 2.5 hours. To the reaction mixture was added ethyl acetate, followed by adjusting to pH 7.5 with a saturated aqueous sodium bicarbonate. The separated organic layer was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave a residue, which was pulverized with diisopropyl ether to obtain benzhydryl 7-[2-(trans-3-tert-butoxycarbonylallyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (4.50 g).

Workup

  1. washThe separated organic layer was washed with a saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the solvent
  4. customgave a residue, which

Sources & evidence

ORD record
ord-00c38cdffa1f40f29c28984c5211005d
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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