Water → 5-(azetidin-1-ylcarbonyl)-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}furan-2-sulfonamide

HRID 1175419Notes

Reaction equation

HRID 1175419 reaction equation
[N:1]1([C:5]([C:7]2[O:11][C:10]([S:12]([NH:15][C:16]3[CH:21]=[C:20]([O:22][C@H:23]([CH3:45])[CH2:24][O:25]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:19]=[C:18]([S:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[C:50]([F:54])[C:49]=4[F:55])[N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(OC)C=CC=CC=1.O>CO>[N:1]1([C:5]([C:7]2[O:11][C:10]([S:12]([NH:15][C:16]3[CH:21]=[C:20]([O:22][C@H:23]([CH3:45])[CH2:24][OH:25])[N:19]=[C:18]([S:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[C:50]([F:54])[C:49]=4[F:55])[N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:8]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 536283645-(azetidin-1-ylcarbonyl)-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-1-methyl-2-(triphenylmethyloxy)ethoxy]pyrimidin-4-yl}furan-2-sulfonamide

Product 1

HCID 115701665-(azetidin-1-ylcarbonyl)-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}furan-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(azetidin-1-ylcarbonyl)-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-1-methyl-2-(triphenylmethyloxy)ethoxy]pyrimidin-4-yl}furan-2-sulfonamide (the product of step iv) (0.24 g) in methanol (5 mL) was added para-toluenesulfonic acid hydrate (58 mg) and anisole (0.34 mL). After stirring at room temperature for 2 d, H2O (5 mL) was added and the mixture extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4), filtered and evaporated to dryness in vacuo. The resulting crude solid was purified by reverse phase HPLC (50% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent) to give the title compound as a white solid. Yield: 10 mg.

Workup

  1. extractionthe mixture extracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customThe resulting crude solid was purified by reverse phase HPLC (50% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent)

Sources & evidence

ORD record
ord-945706927a2b4d3e9bf34e7a07212599
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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