Sodium Hydroxide → HCID 90411711, compound

HRID 1521992Notes

Reaction equation

HRID 1521992 reaction equation
[Cl:1][C:2]1[C:3]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[O:41][CH3:42])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+]>O1CCOCC1.C(O)C.O>[Cl:1][C:2]1[C:3]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[O:41][CH3:42])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 90412743HCID 90412743, compound

Product 1

HCID 90411711HCID 90411711, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 229D (0.16 g, 0.261 mmol) and 3N sodium hydroxide (0.261 mL, 0.784 mmol) in 1,4-dioxane (1.743 mL), ethanol (1.743 mL) and water (0.7 mL) was heated at 75° C. for 2.5 hours. The mixture was concentrated and the residue was partitioned in ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (AnaLogix IntelliFlash 280) eluting with a gradient of from 0-4% methanol in dichloromethane afforded the title compound. MS (ESI+) m/z 458.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned in ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (AnaLogix IntelliFlash 280)
  7. washeluting with a gradient of from 0-4% methanol in dichloromethane

Sources & evidence

ORD record
ord-6fb5456c10fd4c4a9821b2cb517ea83b
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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