Sodium Bicarbonate → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)-1-methylethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

HRID 1958901Notes

Reaction equation

HRID 1958901 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]2([CH3:34])[CH2:31][O:30]C(C)(C)[O:28][CH2:27]2)[N:12]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.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]([CH2:31][OH:30])([CH3:34])[CH2:27][OH:28])[N:12]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 53628343N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2,5-trimethyl-1,3-dioxan-5-yl)oxy]-4-pyrimidinyl]-1-azetidinesulfonamide

Product 1

HCID 11677275N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)-1-methylethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2,5-trimethyl-1,3-dioxan-5-yl)oxy]-4-pyrimidinyl]-1-azetidinesulfonamide (the product from step (0.46 g) in DCM (15 mL) was added iron (III) chloride hexahydrate (0.85 g) and the mixture was stirred and ambient temperature for 30 min. A saturated solution of sodium hydrogencarbonate was added and then extracted with DCM (×4). The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel using a MeOH/DCM (99:1 to 98:2 gradient) as eluent to give the title compound as a white foam. Yield: 100 mg

Workup

  1. extractionextracted with DCM (×4)
  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 using a MeOH/DCM (99:1 to 98:2 gradient) as eluent

Sources & evidence

ORD record
ord-3879f148044c4ae0a296552c44a0e877
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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