Hydrochloric Acid → HCID 178511066, compound

HRID 1902974Notes

Reaction equation

HRID 1902974 reaction equation
Cl.C([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:44][O:45][CH2:46][C:47]([O:49]C(C)(C)C)=[O:48])[C:11]([NH:13][CH:14]2[C:42](=[O:43])[N:16]3[C:17]([C:39]([OH:41])=[O:40])=[C:18]([CH:21]([S:33][C:34]4[NH:38][N:37]=[N:36][N:35]=4)[CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=O>CO>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:44][O:45][CH2:46][C:47]([OH:49])=[O:48])[C:11]([NH:13][CH:14]2[C:42](=[O:43])[N:16]3[C:17]([C:39]([OH:41])=[O:40])=[C:18]([CH:21]([S:33][C:34]4[NH:38][N:37]=[N:36][N:35]=4)[CH2:22][CH2:23][CH2:24][NH2:25])[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451386HCID 178451386, compound

Product 1

HCID 178511066HCID 178511066, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (20.8 g.) was added to a mixture of 7-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(3-tert-butoxycarbonylaminopropyl]-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 39.1 g.) in methanol (400 ml.), and stirred at room temperature for 4 hours. After removing the solvent in vacuo, tetrahydrofuran (40 ml.) and anisole (40 ml.) were added to the residue and stirred at room temperature for 4 hours. The reaction mixture was added to ethyl acetate at room temperature. The precipitates were collected by filtration and washed with ethyl acetate to give 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-[1-(3-aminopropyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (a mixture of syn and anti isomers). The product was subjected to column chromatography on macroporous nonionic absorption resin "HP-20" (trademark, manufactured by Mitsubishi Chemical Industries Co.) to give the syn isomer of the objective compound.

Workup

  1. customAfter removing the solvent in vacuo, tetrahydrofuran (40 ml.) and anisole (40 ml.)
  2. additionwere added to the residue
  3. stirringstirred at room temperature for 4 hours
  4. additionThe reaction mixture was added to ethyl acetate at room temperature
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3578daabcae64ef19b64a4a30da2aabe
Source dataset
uspto-grants-1982_12
Patent number
US04366153

Reaction notes

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