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

HRID 1902965Notes

Reaction equation

HRID 1902965 reaction equation
[ClH:1].C([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:43][O:44][CH2:45][CH2:46][NH:47]C(OC(C)(C)C)=O)[C:11]([NH:13][CH:14]2[C:41](=[O:42])[N:16]3[C:17]([C:38]([OH:40])=[O:39])=[C:18]([CH2:21][S:22][C:23]4[N:27]([CH2:28][CH2:29][NH:30]C(OC(C)(C)C)=O)[N:26]=[N:25][N:24]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=O>CO>[ClH:1].[ClH:1].[ClH:1].[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:43][O:44][CH2:45][CH2:46][NH2:47])[C:11]([NH:13][CH:14]2[C:41](=[O:42])[N:16]3[C:17]([C:38]([OH:40])=[O:39])=[C:18]([CH2:21][S:22][C:23]4[N:27]([CH2:28][CH2:29][NH2:30])[N:26]=[N:25][N:24]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317127737-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317127747-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-[(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid trihydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (3.2 g.) was added to a solution of 7-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 3.5 g.) in methanol (50 ml.) and stirred at room temperature for 2 hours. After removing the solvent in vacuo, methanol was added to the residue. The mixture was concentrated in vacuo again. The precipitates were collected by filtration and washed with diethyl ether to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-[1-(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid trihydrochloride (syn isomer, 2.8 g.)

Workup

  1. customAfter removing the solvent in vacuo, methanol
  2. additionwas added to the residue
  3. concentrationThe mixture was concentrated in vacuo again
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-4a1f39c1c8084976864a4b4a7d4f912f
Source dataset
uspto-grants-1982_12
Patent number
US04366153

Reaction notes

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