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

HRID 255761Notes

Reaction equation

HRID 255761 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:32][O:33][CH2:34][CH2:35][N:36]=[N+:37]=[N-:38])[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.[ClH:39].CO>O1CCCC1>[ClH:39].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:32][O:33][CH2:34][CH2:35][N:36]=[N+:37]=[N-:38])[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 1317152867-[2-(2-Formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152877-[2-(2-Aminothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid hydrochlorideYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.9 g.), conc. hydrochloric acid (0.2 g.), methanol (10 ml.) and tetrahydrofuran (4 ml.) was stirred at room temperature for 5 hours. After concentrating the resultant solution in vacuo, the residue was pulverized with a mixture of disopropyl ether and ethyl acetate (30 ml. 5:1 v/v). The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 0.8 g.).

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. additionthe residue was pulverized with a mixture of disopropyl ether and ethyl acetate (30 ml. 5:1 v/v)
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-a597e81a13e5476091497cf2d6fda03d
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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