Hydrochloric Acid → HCID 131713205, compound

HRID 647732Notes

Reaction equation

HRID 647732 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][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]([CH2:8][CH2:9][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 131713206HCID 131713206, compound

Product 1

HCID 131713205HCID 131713205, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzhydryl 7-[2-(3-tert-butoxycarbonylpropoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (3.5 g), conc. hydrochloric acid (1.0 g), methanol (30 ml) and tetrahydrofuran (15.0 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-(3-tert-butoxycarbonylpropoxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (3.33 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-2fcb5abd7afc440f85a07b1a895f2dd3
Source dataset
uspto-grants-1983_10
Patent number
US04409214

Reaction notes

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