Water → HCID 86704622, compound

HRID 1508573Notes

Reaction equation

HRID 1508573 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[CH:28][C:29]([F:43])=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]([O:40]C)=[O:39])=[CH:34][C:33]=5[CH3:42])[CH:31]=4)=[CH:24][N:23]=[C:22]([S:44][CH3:45])[N:21]=3)[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Li+].[OH-:50].[OH2:51].C1C=C(Cl)C=C(C(OO)=O)C=1>O1CCOCC1>[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[CH:28][C:29]([F:43])=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]([OH:40])=[O:39])=[CH:34][C:33]=5[CH3:42])[CH:31]=4)=[CH:24][N:23]=[C:22]([S:44]([CH3:45])(=[O:51])=[O:50])[N:21]=3)[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86704620HCID 86704620, compound

Product 1

HCID 86704622HCID 86704622, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of the title compound from Step C (150 mg, 0.216 mmol) and LiOH (51.8 mg, 2.16 mmol) was stirred in dioxane and water overnight. The solvent was removed and water was added. A few drops of 1 N HCl were added. The organic material was extracted with EtOAc (3×10 mL). The combined EtOAc layers were dried over Na2SO4. The solvent was removed. The residue was dissolved in CH2Cl2 (5 mL) at 25° C. and mCPBA (82 mg, 0.476 mmol) was added. The solution was stirred at 25° C. for 3 h. The solution was washed with Na2S2O3 and dried over Na2SO4. The residue was purified by reverse phase HPLC to give the title compound as a colorless solid. LCMS=712.6 (M+H)+

Workup

  1. customThe solvent was removed
  2. additionwater was added
  3. additionA few drops of 1 N HCl were added
  4. extractionThe organic material was extracted with EtOAc (3×10 mL)
  5. dry with materialThe combined EtOAc layers were dried over Na2SO4
  6. customThe solvent was removed
  7. dissolutionThe residue was dissolved in CH2Cl2 (5 mL) at 25° C.
  8. washThe solution was washed with Na2S2O3
  9. dry with materialdried over Na2SO4
  10. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9a3e21d8f4d64678a80aed1fc22d8b89
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

Loading…