Hydrochloric Acid → 7-[2-(2-Aminothiazol-4yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid

HRID 1462822Notes

Reaction equation

HRID 1462822 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.CO>O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1317124997-[2-(2-Formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid

Product 1

HCID 1317125007-[2-(2-Aminothiazol-4yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 2.4 g.), conc.hydrochloric acid (1.84 g.), methanol (36 ml.) and tetrahydrofuran (30 ml.) was stirred at 30° C. for 2 hours. The resultant solution was concentrated in vacuo. Water (60 ml.) was added to the residue and the precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.86 g.).

Workup

  1. concentrationThe resultant solution was concentrated in vacuo
  2. additionWater (60 ml.) was added to the residue
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-547ec74279004af9b8affcbd9eff8fe6
Source dataset
uspto-grants-1984_07
Patent number
US04460583

Reaction notes

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