Sodium Acetate → HCID 178501867, compound

HRID 1262764Notes

Reaction equation

HRID 1262764 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].[NH2:29][C:30]([NH2:32])=[S:31].C([O-])(=O)C.[Na+]>O1CCCC1.O>[NH2:32][C:30]1[S:31][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:29]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 178501866HCID 178501866, compound

Product 1

HCID 178501867HCID 178501867, compoundYield 73.4%

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) (2.6 g), thiourea (0.91 g) and sodium acetate (2.46 g) in tetrahydrofuran (10 ml) and water (20 ml) was stirred at 40° to 45° C. for 3 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 2.2 with 10% hydrochloric acid and the acidified aqueous solution was extracted with ethyl acetate-tetrahydrofuran (8:2). The organic 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-aminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (2.0 g).

Workup

  1. washthe resultant solution was washed with ethyl acetate
  2. extractionthe acidified aqueous solution was extracted with ethyl acetate-tetrahydrofuran (8:2)
  3. washThe organic 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-9c5d2f3406f04a4db7924467fe7974d7
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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