Thionyl Chloride → HCID 131722868, compound

HRID 1597169Notes

Reaction equation

HRID 1597169 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][S:36][C:37]1[S:38][C:39]2[CH:47]=[C:46]([CH2:48]O)[CH:45]=[CH:44][C:40]=2[C:41](=[O:43])[CH:42]=1)=[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.S(Cl)([Cl:52])=O>C1C=CC=CC=1>[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][S:36][C:37]1[S:38][C:39]2[CH:47]=[C:46]([CH2:48][Cl:52])[CH:45]=[CH:44][C:40]=2[C:41](=[O:43])[CH:42]=1)=[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

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131722869HCID 131722869, compound

Product 1

HCID 131722868HCID 131722868, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7β-Tert-butoxycarbonylamino-3-[2-(7-hydroxymethyl-4-oxo-4H-1-benzothiopyran-2-yl)thiovinyl]-3-cephem-4-carboxylic acid benzhydryl ester (330 mg, 0.46 mmol) was suspended in anhydrous benzene (10 ml), added dropwise with thionyl chloride (0.55 ml, 7.59 mmol) while stirred at room temperature. Then, the reaction mixture was stirred at 50 minutes, added with ice water and extracted with ethyl acetate (50 ml). Ethyl acetate layer was washed with saturated saline solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was crystallized from isopropyl ether to obtain 300 mg (yield: 89%) of 7β-tert-butoxycarbonylamino-3-[2(7-chloromethyl-4-oxo-4H-1-benzothiopyran-2-yl)thiovinyl]-3-cephem-4-carboxylic acid benzhydryl ester. Further, the process similar to that shown in (2) of the Example 1 was conducted to obtain 160 mg (yield: 62%) of the titled compound.

Workup

  1. stirringThen, the reaction mixture was stirred at 50 minutes
  2. extractionextracted with ethyl acetate (50 ml)
  3. washEthyl acetate layer was washed with saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-e33ea9821f3b456899dfbf571be7d0db
Source dataset
uspto-grants-2001_09
Patent number
US06294527B1

Reaction notes

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