Sodium Bicarbonate → HCID 67742847, compound

HRID 655052

Reaction equation

HRID 655052 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30]Cl)=[O:10])=[CH:5][CH:4]=1.[SH:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:22]1([CH2:21][C:20]([NH:19][C@@H:18]2[C:17](=[O:29])[N:16]3[C:11]([C:9]([O:8][CH2:7][C:6]4[CH:32]=[CH:33][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[O:10])=[C:12]([CH2:30][S:34][C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)[CH2:13][S:14][C@H:15]23)=[O:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 178418431pyridine-4-thiol

Product 1

HCID 67742847HCID 67742847, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred and ice cold solution of 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) (4.87 g; 10 mMol.) and 4-mercaptopyridine (1.45 g; 1.3 Eq.) in N,N-dimethylformamide (15 ml) is added sodium hydrogen carbonate (1.09 g; 1.3 Eq.), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with ice water and separating solidis collected by filtration, dissolved in ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue is washed with ether to give p-methoxybenzyl 7β-phenylacetamido-3-(4-pyridyl)thiomethyl-3-cephem-4-carboxylate (2) (5.25 g).

Workup

  1. stirringthe mixture is stirred at room temperature for 1 hour
  2. customseparating solidis
  3. filtrationcollected by filtration
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. washThe residue is washed with ether

Sources & evidence

ORD record
ord-0f834af4318a40a9b90f1c12f6e11c4a
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Linked notes

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