Water → HCID 24765776, compound

HRID 1255146Notes

Reaction equation

HRID 1255146 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[C:10]([C:12](N(OC)C)=[O:13])[N:11]=1)=[O:5].C[Mg+].[Br-].O.[CH2:37]1COC[CH2:38]1>>[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)=[C:10]([C:12](=[O:13])[CH2:37][CH3:38])[N:11]=1)=[O:5]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24765775HCID 24765775, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 24765776HCID 24765776, compoundYield 83%

Procedure

To the solution of Compound 93 (220 mg, 0.47 mmol) in 10 mL of anhydrous THF was added MeMgBr (3.0 M in Et2O, 0.5 mL) at −78° C. The solution was slowly warmed to room temperature over 2 hours. The reaction mixture was treated with 10 mL of water. The mixture was extracted with Et2O, the combined organic phases were dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (eluted with 10-100% ethyl acetate in hexanes) to give Compound 94 (184 mg, 83%) as a white solid.

Workup

  1. extractionThe mixture was extracted with Et2O
  2. dry with materialthe combined organic phases were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (eluted with 10-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-940a2bfd0e9a475d80f49da6a4153546
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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