Hydrochloric Acid → 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255784Notes

Reaction equation

HRID 255784 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][CH2:36][NH:37]C(OC(C)(C)C)=O)[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][CH2:36][NH2:37])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317153147-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317134767-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.6 g.), conc. hydrochloric acid (2 g.) and methanol (40 ml.) was stirred at room temperature for 3 hours. After evaporating the solvent in vacuo, methanol was added to the residue and mixture was evaporated in vacuo again. The residue was dissolved in water (30 ml.) and adjusted to pH 3.5 with a saturated sodium bicarbonate aqueous solution under ice-cooling. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" [trademark, manufactured by Mitsubishi Chemical Industries Ltd.], and eluted with 30% aqueous isopropyl alcohol. The eluate was concentrated in vacuo and the residue was lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.7 g.)

Workup

  1. customAfter evaporating the solvent in vacuo, methanol
  2. additionwas added to the residue and mixture
  3. customwas evaporated in vacuo again
  4. dissolutionThe residue was dissolved in water (30 ml.)
  5. temperaturecooling
  6. wash" [trademark, manufactured by Mitsubishi Chemical Industries Ltd.], and eluted with 30% aqueous isopropyl alcohol
  7. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-61d5ac810ec94730b01d3a852b9e0e73
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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