Hydrochloric Acid → HCID 131713174, compound

HRID 1656205Notes

Reaction equation

HRID 1656205 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:21]1[C:46](=[O:47])[N:23]2[C:24]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[C:25]([CH:28]=[CH2:29])[CH2:26][S:27][C@H:22]12)[C:9](=[O:20])[CH:10]([C:12]1[N:13]=[C:14]([NH:17]C=O)[S:15][CH:16]=1)[NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH:21]1[C:46](=[O:47])[N:23]2[C:24]([C:30]([O:32][CH:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:31])=[C:25]([CH:28]=[CH2:29])[CH2:26][S:27][C@H:22]12)[C:9](=[O:20])[CH:10]([C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1)[NH2:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131718221HCID 131718221, compound

Product 1

HCID 131713174HCID 131713174, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzhydryl 7-[N-tert-butoxycarbonyl-2-(2-formamidothiazol-4-yl)glycinamido]-3-vinyl-3-cephem-4-carboxylate (5.6 g) and conc. hydrochloric acid (2.6 ml) in methanol (60 ml) and tetrahydrofuran (15 ml) was stirred at ambient temperature for 2.5 hours. The precipitated substance in the reaction mixture was collected by filtration, and washed with a mixture of methanol and water (1:2 by volume) and then water, followed by drying to give benzhydryl 7-[N-tert-butoxycarbonyl-2-(2-aminothiazol-4-yl)glycinamido]-3-vinyl-3-cephem-4-carboxylate (0.4 g).

Workup

  1. filtrationThe precipitated substance in the reaction mixture was collected by filtration
  2. washwashed with a mixture of methanol and water (1:2 by volume)
  3. customby drying

Sources & evidence

ORD record
ord-caa1d0b7d1254cb1a6ee118619340d44
Source dataset
uspto-grants-1993_10
Patent number
US05252731

Reaction notes

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