Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid trihydrochloride

HRID 1154130Notes

Reaction equation

HRID 1154130 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:41][O:42][CH2:43][CH2:44][NH:45]C(OC(C)(C)C)=O)[C:10]([NH:12][CH:13]2[C:39](=[O:40])[N:15]3[C:16]([C:36]([OH:38])=[O:37])=[C:17]([CH2:20][S:21][C:22]4[S:23][C:24]([CH2:27][NH:28]C(OC(C)(C)C)=O)=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:53]>CO>[ClH:53].[ClH:53].[ClH:53].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:41][O:42][CH2:43][CH2:44][NH2:45])[C:10]([NH:12][CH:13]2[C:39](=[O:40])[N:15]3[C:16]([C:36]([OH:38])=[O:37])=[C:17]([CH2:20][S:21][C:22]4[S:23][C:24]([CH2:27][NH2:28])=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317127767-[2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-(5-tert-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317127777-[2-(2-Aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid trihydrochlorideYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-[2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-(5-tert-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 3.7 g.), conc. hydrochloric acid (2.9 g.) and methanol (50 ml.) were treated in a similar manner to that of Example 8-(2) to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid trihydrochloride (syn isomer, 2.9 g.).

Sources & evidence

ORD record
ord-b64d254b4d36465db51f0d50314e5c7e
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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