Water → HCID 59558745, compound

HRID 2388815Notes

Reaction equation

HRID 2388815 reaction equation
[F:1][C:2]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([NH:12][S:13]([N:16]2[CH2:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:20][C@H:21]([C@H:23]2[CH2:27][O:26]C3(CCCCC3)[O:24]2)[CH3:22])[N:7]=1.O>C(Cl)Cl.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[F:1][C:2]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([NH:12][S:13]([N:16]2[CH2:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:20][C@@H:21]([CH3:22])[C@H:23]([OH:24])[CH2:27][OH:26])[N:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 53628372HCID 53628372, compound

Product 1

HCID 59558745HCID 59558745, compound

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(2-[(2,3-difluorobenzyl)thio]-6-{(1S)-1-[(2R)-1,4-dioxaspiro[4.5]dec-2-yl]ethoxy}pyrimidin-4-yl)azetidine-1-sulfonamide (the product of step (43 mg) in DCM (4 ml) was added iron (III) chloride hexahydrate (73 mg). The reaction mixture was stirred at room temperature for 2 h after which time further iron (III) chloride hexahydrate (40 mg) was added. After 3 d at −18° C., H2O and DCM were added. The layers were separated and the aqueous material extracted with further DCM. The combined organic extracts were washed with saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated. TFA (1 ml) and DCM (4 ml) were added to the residue and the reaction mixture stirred at room temperature for 2 d. The mixture was partitioned between saturated aqueous sodium bicarbonate and DCM, then neutralised with 2 M aqueous hydrochloric acid, the layers separated and the aqueous material extracted with further DCM. The DCM extracts were allowed to slowly evaporate and the resulting solid washed with minimal cold DCM to afford the title compound as a white powder. Yield: 11 mg

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous material extracted with further DCM
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. additionTFA (1 ml) and DCM (4 ml) were added to the residue
  9. customThe mixture was partitioned between saturated aqueous sodium bicarbonate and DCM
  10. customthe layers separated
  11. extractionthe aqueous material extracted with further DCM
  12. customto slowly evaporate
  13. washthe resulting solid washed with minimal cold DCM

Sources & evidence

ORD record
ord-b6b2b2d27e744807a48df79736448e25
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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