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

HRID 255770Notes

Reaction equation

HRID 255770 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][C:36]#[N: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)=O.Cl>CO.O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][C:36]#[N: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1317152977-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152987-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 64.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.05 g.) and conc. hydrochloric acid (1.52 g.) in methanol (30 ml.) and tetrahydrofuran (20 ml.) was stirred at room temperature for 2 hours. After the solvent was evaporated in vacuo, the residue was dissolved in 10% aqueous solution of sodium hydroxide. After filtration, the filtrate was adjusted to pH 3.0 with 10% hydrochloric acid and stirred under ice-cooling for 30 minutes. The precipitates were collected by filtration, washed with water and dried to give 7-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.25 g.).

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 10% aqueous solution of sodium hydroxide
  3. filtrationAfter filtration
  4. temperaturecooling for 30 minutes
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-5e039d17eb674230b10f48197cb59b13
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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