Sodium Acetate → HCID 131715003, compound

HRID 1249424Notes

Reaction equation

HRID 1249424 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:36][O:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:5]([NH:7][CH:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:12](/[CH:15]=[CH:16]/[Cl:17])[CH2:13][S:14][C@H:9]12)=[O:6].[NH2:44][C:45]([NH2:47])=[S:46].C([O-])(=O)C.[Na+]>O1CCCC1.O>[CH3:42][O:41][C:39]([CH2:38][O:37][N:36]=[C:4]([C:3]1[N:44]=[C:45]([NH2:47])[S:46][CH:2]=1)[C:5]([NH:7][CH:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20][CH:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:19])=[C:12](/[CH:15]=[CH:16]/[Cl:17])[CH2:13][S:14][C@H:9]12)=[O:6])=[O:40]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 131715004HCID 131715004, compound

Product 1

HCID 131715003HCID 131715003, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7-(4-chloro-2-methoxycarbonylmethoxyimino-3-oxobutyramido)-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (1.65 g) in a mixture of tetrahydrofuran (10 ml) and water (10 ml) were added thiourea (0.39 g) and sodium acetate (1.05 g). The mixture was stirred at ambient temperature for 2 hours and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was triturated with diisopropyl ether and collected by filtration to give benzhydryl 7-[2-methoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (1.45 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2f33fa1e58c64d76ac7bacb48ae5d20b
Source dataset
uspto-grants-1986_12
Patent number
US04631274

Reaction notes

Loading…