Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acid

HRID 745428Notes

Reaction equation

HRID 745428 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[C:30]([OH:35])[CH:29]=2)[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.CO>O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[C:30]([OH:35])[CH:29]=2)[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131712351HCID 131712351, compound

Product 1

HCID 1317123527-[2-(2-Aminothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.0 g.), conc. hydrochloric acid (1.1 g.), methanol (16 ml.) and tetrahydrofuran (10 ml.) was stirred at room temperature for 2 hours. After methanol was removed in vacuo, the residue was dissolved in a sodium bicarbonate aqueous solution and adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorous pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.6 g.).

Workup

  1. customAfter methanol was removed in vacuo
  2. dissolutionthe residue was dissolved in a sodium bicarbonate aqueous solution
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-9feaedbf65ba4ef3960b7016e3f881d8
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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