HCID 67051212, compound → HCID 59558749, compound

HRID 1958898Notes

Reaction equation

HRID 1958898 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][C:26]([C@H:29]2[CH2:33][O:32]C(C)(C)[O:30]2)([CH3:28])[CH3:27])[N:12]=1>C(Cl)Cl.C(=O)([O-])O.[Na+].O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][C:26]([CH3:28])([CH3:27])[C@H:29]([OH:30])[CH2:33][OH:32])[N:12]=1

Participants

5

Reactant 1

HCID 67051212HCID 67051212, compound

Product 1

HCID 59558749HCID 59558749, compound

Reagents, catalysts & solvents 3

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methylethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide (the product from step iii) 0.34 g) in DCM (9 mL) was added iron (III) chloride hexahydrate (0.61 g) and the mixture was stirred at ambient temperature for 35 min. The reaction mixture was diluted with sat. sodium hydrogencarbonate solution and extracted with DCM (×3). The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel using MeOH/DCM (99:1 to 98:2 gradient) as eluent to give the title compound as a white foam. Yield: 0.20 g

Workup

  1. extractionextracted with DCM (×3)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-93f73d4370ed4224a90c7961d63b169f
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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