Sodium Acetate → HCID 178482390, compound

HRID 1262765Notes

Reaction equation

HRID 1262765 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:21][O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:5]([NH:7][CH:8]1[C:19](=[O:20])[N:10]2[C:11]([C:16]([OH:18])=[S:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]12)=[O:6].[CH3:29][NH:30][C:31]([NH2:33])=[S:32].C([O-])(=O)C.[Na+]>O.O1CCCC1>[CH3:29][NH:30][C:31]1[S:32][CH:2]=[C:3]([C:4](=[N:21][O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:5]([NH:7][CH:8]2[C:19](=[O:20])[N:10]3[C:11]([C:16]([OH:18])=[S:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]23)=[O:6])[N:33]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723704MethylthioureaHCID 178501866HCID 178501866, compound

Product 1

HCID 178482390HCID 178482390, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[4-chloro-2-(methoxycarbonylmethoxyimino)-3-oxobutyramido]-3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (4.3 g), N-methylthiourea (1.8 g) and sodium acetate (4.1 g) in water (20 ml) and tetrahydrofuran (40 ml) was stirred at 38° to 42° C. for 2.5 hours. Water (50 ml) was added to the reaction mixture and the resultant solution was washed with ethyl acetate. The separated aqueous layer was acidified to pH 2.3 with 10% hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over magnesium sulfate. The solution was evaporated and the residue was triturated with ether to give 7-[2-(2-methylaminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (3.2 g).

Workup

  1. washthe resultant solution was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-c6ea36947b054a5ebe705951833f3166
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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