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 1154128Notes

Reaction equation

HRID 1154128 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-a4909873b01f45c395331a9151f137a8
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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