Sodium Iodide → HCID 141558884, compound

HRID 653562Notes

Reaction equation

HRID 653562 reaction equation
[C:1]([O:5][C:6]([C:8]1([O:11]/[N:12]=[C:13](/[C:44]2[N:45]=[C:46]([NH:49][C:50]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[S:47][CH:48]=2)\[C:14]([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[C:20]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:21]([CH2:24]Cl)[CH2:22]S[C@H:18]23)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[S:80]([O-:84])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+].[I-:92].[Na+]>C(Cl)Cl.CC(C)=O.C(OCC)(=O)C.CCCCCC>[C:1]([O:5][C:6]([C:8]1([O:11]/[N:12]=[C:13](/[C:44]2[N:45]=[C:46]([NH:49][C:50]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[S:47][CH:48]=2)\[C:14]([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[C:20]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:21]([CH2:24][I:92])[CH2:22][S:80](=[O:84])[C@H:18]23)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 141551541HCID 141551541, compound

Product 1

HCID 141558884HCID 141558884, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

14.2 g (14.7 mmol) of benzhydryl 7-[(Z)-2-(1-tertbutoxycarbonyl-1-cyclopropoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate was dissolved in 280 ml of methylene chloride, and 2.98 g (14.7 mmol) of m-chloroperbenzoic acid was added thereto under cooling with ice. The mixture was stirred for 10 minutes. To the reaction solution, 60 ml of a 10% sodium thiosulfate aqueous solution was added. The aqueous solution was poured into a 5% sodium hydrogen carbonate aqueous solution, then extracted with methylene chloride and dried over anhydrous sodium sulfate. The residue obtained by the concentration under reduced pressure was dissolved in 300 ml of acetone, and then 4.4 g (29.4 mmol) of sodium iodide was added thereto at 0° C. The mixture was stirred at room temperature for 15 minutes. The reaction solution was washed with a sodium thiosulfate aqueous solution and with a saturated sodium chloride aqueous solution. Then the organic solvent layer was dried over anhydrous sodium sulfate. The residue obtained by the concentration under reduced pressure was subjected to silica gel flush column chromatography (ethyl acetate/n-hexane=1/2) to obtian 9.52 g (yield: 60%) of the above-identified compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by the concentration under reduced pressure
  5. customat 0° C
  6. stirringThe mixture was stirred at room temperature for 15 minutes
  7. washThe reaction solution was washed with a sodium thiosulfate aqueous solution and with a saturated sodium chloride aqueous solution
  8. dry with materialThen the organic solvent layer was dried over anhydrous sodium sulfate
  9. customThe residue obtained by the concentration under reduced pressure

Sources & evidence

ORD record
ord-8b5830f163ab4a7abd43a33f78bc98d2
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

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