Iodine → HCID 22844776, compound

HRID 893576Notes

Reaction equation

HRID 893576 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:13]1)[N:8]1[CH:24]([CH3:26])[S:25][C:7]1=[C:6]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:5]2=[O:32].II.[Cl:35]S(O)(=O)=O>>[Cl:35][C:10]1[C:11]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:23])[C:19]([F:21])([F:20])[F:22])[CH2:13]2)=[C:2]([F:1])[CH:3]=[C:4]2[C:9]=1[N:8]1[CH:24]([CH3:26])[S:25][C:7]1=[C:6]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:5]2=[O:32]

Participants

4

Reactant 3

HCID 807IodineHCID 24638Chlorosulfonic acidHCID 86745952HCID 86745952, compound

Product 1

HCID 22844776HCID 22844776, compound

Procedure

To a solution of 1.50 g of ethyl 6-fluoro-1-methyl-4-oxo-7-((S)-3-trifluoroacetylamino-1-pyrrolidinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate in 4.0 ml of chlorosulfonic acid, a trace of iodine was added, and the mixture was bubbled with chlorine gas for 1 hour under ice cooling with stirring. The reaction mixture was poured into ice water and was extracted with chloroform. The extract was washed with aqueous potassium carbonate and water, dried and evaporated. The residue was chromatographed on silica gel using chloroform-methanol (50:1) as an eluent to give 1.61 g of the desired compound, which was recrystallized from a mixture of ethyl acetate and diisopropyl ether. The obtained crystals were consistent with that of Example 1.

Workup

  1. customthe mixture was bubbled with chlorine gas for 1 hour under ice cooling
  2. additionThe reaction mixture was poured into ice water
  3. extractionwas extracted with chloroform
  4. washThe extract was washed with aqueous potassium carbonate and water
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f65104b14d3b423d8c60992ff7283148
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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