Ethyl Acetate → HCID 131722866, compound

HRID 1597168Notes

Reaction equation

HRID 1597168 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:33])[C@@H:24]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:21]2[S:20][CH2:19][C:18]=1[CH:34]=[CH:35]OS(C(F)(F)F)(=O)=O)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:44][C:45]1[S:46][C:47]2[CH:55]=[CH:54][CH:53]=[CH:52][C:48]=2[C:49](=[O:51])[CH:50]=1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>CN(C=O)C>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:33])[C@@H:24]([NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[C@H:21]2[S:20][CH2:19][C:18]=1[CH:34]=[CH:35][S:44][C:45]1[S:46][C:47]2[CH:55]=[CH:54][CH:53]=[CH:52][C:48]=2[C:49](=[O:51])[CH:50]=1)=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 13906436HCID 13906436, compoundHCID 131722867HCID 131722867, compound

Product 1

HCID 131722866HCID 131722866, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7β-Tert-butoxycarbonylamino-3-(2-trifluoromethanesulfonyloxyvinyl)-3-cephem-4-carboxylic acid benzhydryl ester (trans isomer) (3.9 g, 6.1 mmol) was dissolved in anhydrous DMF (80 ml), added with 2-mercapto-4-oxo-4H-1-benzothiopyran (3.5 g, 18.3 mmol) and N-ethyldiisopropylamine (0.63 g, 4.87 mmol), successively, and stirred at room temperature under argon gas atmosphere for 24 hours. The reaction product was added with ethyl acetate (350 ml), washed with an aqueous solution of saturated sodium hydrogencarbonate (150 ml×2 times) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (Wago Gel™ C-200, methylene chloride-ethyl acetate (8:1)) to obtain 3.56 g (yield: 85.4%) of 7β-tert-butoxycarbonylamino-3-[2-(4-oxo-4H-1-benzothiopyran-2-yl)thiovinyl]-3-cephem-4-carboxylic acid benzhydryl ester as yellow-red froth.

Workup

  1. washwashed with an aqueous solution of saturated sodium hydrogencarbonate (150 ml×2 times)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (Wago Gel™ C-200, methylene chloride-ethyl acetate (8:1))

Sources & evidence

ORD record
ord-47bdfa4bb73c431a8d3f4b95a628c1d3
Source dataset
uspto-grants-2001_09
Patent number
US06294527B1

Reaction notes

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