Hydrochloric Acid → HCID 131713186, compound

HRID 1381431Notes

Reaction equation

HRID 1381431 reaction equation
C([NH:3][C:4]1[S:5][C:6]([C:9](=[N:27][O:28][CH3:29])[C:10]([NH:12][CH:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])=[CH:7][N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][C:6]([C:9](=[N:27][O:28][CH3:29])[C:10]([NH:12][CH:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 137175473HCID 137175473, compound

Product 1

HCID 131713186HCID 131713186, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-5-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.9 g) and conc. hydrochloric acid (1.36 g) in methanol (190 ml) was stirred at ambient temperature for 1.3 hours. After the reaction mixture was evaporated to dryness, the residue was suspended in water (35 ml) and then adjusted to pH 7-8 with 10% aqueous sodium hydroxide, followed by adjusting to pH 3 with 10% hydrochloric acid. The precipitated solid was collected by filtration, washed with water and then dried to give 7-[2-(2-aminothiazol-5-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.3 g), mp >250° C.

Workup

  1. customAfter the reaction mixture was evaporated to dryness
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-9c6da0e33bd843caacdd351542655d79
Source dataset
uspto-grants-1986_04
Patent number
US04585860

Reaction notes

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