Water → HCID 70265609, compound

HRID 1858526Notes

Reaction equation

HRID 1858526 reaction equation
[NH2:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([S:9]/[CH:10]=[CH:11]/[C:12]3[CH:13]=[N:14][NH:15][CH:16]=3)[CH2:7][S:8][C@H:3]12.C[Si](C)(C)N[C:38](=[O:40])[CH3:39].[C:43]1([CH2:49][C:50](Cl)=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.O>O1CCCC1.C(OCC)(=O)C>[C:21]1([CH2:39][C:38]([NH:1][C@@H:2]2[C:33](=[O:34])[N:4]3[C:5]([C:17]([O:19][CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:18])=[C:6]([S:9]/[CH:10]=[CH:11]/[C:12]4[CH:13]=[N:14][N:15]([C:50]([CH2:49][C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)=[O:51])[CH:16]=4)[CH2:7][S:8][C@H:3]23)=[O:40])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 70265824HCID 70265824, compound

Product 1

HCID 70265609HCID 70265609, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7β-amino-3-[(E)-2-(4-pyrazolyl)vinylthio]-3-cephem-4-carboxylate (515 mg) in tetrahydrofuran (12.5 ml) was added N-trimethylsilylacetamide (550 mg), and stirred at room temperature for 15 minutes. To the solution was added dropwise a solution of phenylacetyl chloride (146 μl) above at -20° C. for 2 minutes. The mixture was stirred at -20~-15° C. for 1 hour. To the reaction mixture were added water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with buffer solution (pH 7) and saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was subjected to column chromatography on silica gel (eluent: dichloromethane:ethyl acetate=9:1) to give benzhydryl 7β-(2-phenylacetamido)-3-[(E)-2-(1-benzylcarbonylpyrazol-4-yl)vinylthio]-3-cephem-4-carboxylate (93.4 mg).

Workup

  1. stirringThe mixture was stirred at -20~-15° C. for 1 hour
  2. customThe organic layer was separated
  3. washwashed with buffer solution (pH 7) and saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb0d04dd7b514926bada971f42967dbe
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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