Ethyl Acetate → HCID 131713542, compound

HRID 1262763Notes

Reaction equation

HRID 1262763 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:34][O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:5]([NH:7][CH:8]1[C:32](=[O:33])[N:10]2[C:11]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[S:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]12)=[O:6].[NH2:42][C:43]([NH2:45])=[S:44].C([O-])(=O)C.[Na+].C(OCC)(=O)C>O1CCCC1.O>[NH2:45][C:43]1[S:44][CH:2]=[C:3]([C:4](=[N:34][O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:5]([NH:7][CH:8]2[C:32](=[O:33])[N:10]3[C:11]([C:16]([O:18][CH:19]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[S:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]23)=[O:6])[N:42]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 131713527HCID 131713527, compound

Product 1

HCID 131713542HCID 131713542, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzhydryl 7-[4-chloro-2-(methoxycarbonylmethoxyimino)-3-oxobutyramido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (18.97 g), thiourea (4.56 g) and sodium acetate (7.38 g) in tetrahydrofuran (150 ml) and water (80 ml) was stirred at 40° to 45° C. for 2 hours. Ethyl acetate (300 ml) was added to the reaction mixture at room temperature and the organic layer was separated. 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 benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (17.5 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solution was evaporated
  5. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-8dd31b250001480aa91955870ed78a17
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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