diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → Diphenylmethyl (6R,7R)-8-oxo-7-((phenylacetyl)amino)-3-((4-(pyridin-4-yl)-1,3-thiazol-2-yl)thio)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

HRID 1071314Notes

Reaction equation

HRID 1071314 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:13])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[C:14]1([CH2:20][C:21]([NH:23][C@@H:24]2[C:52](=[O:53])[N:26]3[C:27]([C:36]([O:38][CH:39]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:37])=[C:28](OS(C)(=O)=O)[CH2:29][S:30][C@H:25]23)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.[Cl-].[Na+].O>[C:14]1([CH2:20][C:21]([NH:23][C@@H:24]2[C:52](=[O:53])[N:26]3[C:27]([C:36]([O:38][CH:39]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)=[O:37])=[C:28]([S:13][C:10]4[S:11][CH:12]=[C:8]([C:5]5[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=5)[N:9]=4)[CH2:29][S:30][C@H:25]23)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 11050121diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178527847HCID 178527847, compound

Product 1

HCID 68808181Diphenylmethyl (6R,7R)-8-oxo-7-((phenylacetyl)amino)-3-((4-(pyridin-4-yl)-1,3-thiazol-2-yl)thio)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Pyridyl)-1,3-thiazole-2-thiol sodium salt (194 g, 1 mol) prepared according to the method of Reference Example 5 was suspended in tetrahydrofuran (1.5 L) and benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate (196 g, 0.91 mol) dissolved in tetrahydrofuran (3.0 L) was added dropwise under ice-cooling over 30 min. The mixture was stirred at 0° C. for 2 hr and saturated brine (7 L) was added. The mixture was extracted with ethyl acetate (5 L). The organic layer was washed with saturated brine (5 L) and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give the title compound as crystals. The crystals were suspended in ethyl acetate (0.5 L), collected by filtration on a glass filter and washed with methanol (1 L×2). The crystals were dried in vacuo to give the title compound (412 g, 0.71 mol). yield: 78%.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling over 30 min
  3. extractionThe mixture was extracted with ethyl acetate (5 L)
  4. washThe organic layer was washed with saturated brine (5 L)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc071772bb0c470b8fbbcbef5a42e816
Source dataset
uspto-grants-2005_06
Patent number
US06906055B2

Reaction notes

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