Hydrochloric Acid → HCID 178480374, compound

HRID 1614088Notes

Reaction equation

HRID 1614088 reaction equation
FC(F)(F)C([O-])=O.[CH:8]1([O:13][N:14]=[C:15]([C:51]2[N:52]=[C:53]([NH:56]C=O)[S:54][CH:55]=2)[C:16]([NH:18][C@@H:19]2[C:49](=[O:50])[N:21]3[C:22]([C:33]([O:35][CH:36]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])=[C:23]([CH2:26][N+:27]4[N:28]([CH3:32])[CH:29]=[CH:30][CH:31]=4)[CH2:24][S:25][C@H:20]23)=[O:17])[CH2:12][CH2:11][CH:10]=[CH:9]1.[ClH:59].O.C(=O)(O)[O-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[Cl-:59].[NH2:56][C:53]1[S:54][CH:55]=[C:51]([C:15](=[N:14][O:13][CH:8]2[CH2:12][CH2:11][CH:10]=[CH:9]2)[C:16]([NH:18][C@@H:19]2[C:49](=[O:50])[N:21]3[C:22]([C:33]([O:35][CH:36]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])=[C:23]([CH2:26][N+:27]4[N:28]([CH3:32])[CH:29]=[CH:30][CH:31]=4)[CH2:24][S:25][C@H:20]23)=[O:17])[N:52]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 178480372HCID 178480372, compound

Product 1

HCID 178480374HCID 178480374, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of benzhydryl 7β-[2-(2-cyclopenten-1-yloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trifluoroacetate (syn isomer, 4.9 g) in a mixture of methanol (50 ml) and tetrahydrofuran (10 ml)was added conc. hydrochloric acid (2.13 g) and the mixture was stirred at ambient temperature for 3 hours. Water (50 ml) and ethyl acetate (50 ml) were added thereto and the mixture was adjusted to pH 7.0 with 5% aqueous solution of sodium bicarbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated to give benzhydryl 7β-[2-(2-aminothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride (syn isomer, 3.66 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-9b9e17f5b3bf41f78d466b7c19b55086
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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