Ethanol → HCID 59639635, compound

HRID 556625Notes

Reaction equation

HRID 556625 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[C:10]=3[N:11]=[C:12](S(C)(=O)=O)[N:13]=2)=[C:4]([CH3:30])[CH:3]=1.[H-].[Na+].[CH3:33][CH2:34][OH:35]>>[CH2:34]([O:35][C:12]1[N:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:30])[C:9]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:10]=2[N:11]=1)[CH3:33]

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydride2×HCID 10113314HCID 10113314, compound

Product 1

HCID 59639635HCID 59639635, compound

Procedure

The product of Example 59 (200 mg, 0.47 mmol) was placed in EtOH (10 mL) and the mixture stirred under Ar. Approximately 2 mL of the ethanol was distilled off to dry the mixture. When the mixture was cooled to 23°, some of the starting material sulfone crystallized out. NaH (11.5 mg, 0.46 mmol) was added. The reaction did not go to completion, so additional NaH (4 mg, 0.16 mmol) was added. The solvent was removed in vacuo, and the residue was flash chromatographed on silica gel eluted with 60-100% CH2Cl2/hexane. Recrystallization from CH2Cl2/hexane gave the title compound as a white crystalline solid. mp 137-139°, LC MS m/z=394(MH+) Retention time=2.32 min.

Workup

  1. distillationApproximately 2 mL of the ethanol was distilled off
  2. customto dry the mixture
  3. temperatureWhen the mixture was cooled to 23°
  4. customsome of the starting material sulfone crystallized out
  5. additionwas added
  6. customThe solvent was removed in vacuo
  7. customchromatographed on silica gel
  8. washeluted with 60-100% CH2Cl2/hexane
  9. customRecrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-d100dd75991a48c78df0d2213f37af35
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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