Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255756Notes

Reaction equation

HRID 255756 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:32][O:33][CH2:34][C:35]#[N:36])[C:10]([NH:12][CH:13]2[C:30](=[O:31])[N:15]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[S:23][CH:24]=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.CO.Cl>O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:32][O:33][CH2:34][C:35]#[N:36])[C:10]([NH:12][CH:13]2[C:30](=[O:31])[N:15]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[S:23][CH:24]=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1317152817-[2-(2-Formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152827-[2-(2-Aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.8 g.), methanol (12 ml.), conc hydrochloric acid (0.55 g.) and tetrahydrofuran (10 ml.) was stirred at room temperature for 3 hours. After concentrating the resultant solution in vacuo, the residue was dissolved in an aqueous solution of sodium bicarbonate. The solution was adjusted to pH 3.5 with 10% hydrochloric acid and stirred 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-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.56 g.).

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. dissolutionthe residue was dissolved in an aqueous solution of sodium bicarbonate
  3. stirringstirred for 30 minutes
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0a8c94f5056d452f91f1876a14eb387e
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

Loading…