HCID 58786609, compound → HCID 58786639, compound

HRID 1376063Notes

Reaction equation

HRID 1376063 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21]#N)[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([Mg]Br)[CH:24](C)[CH3:25]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:21][CH:24]([CH3:25])[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 58786609HCID 58786609, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 58786639HCID 58786639, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of product from Step I (750 mg, 2.44 mmol) in THF (15 mL) and isobutylmagnesium bromide (6.1 mL, 12.2 mmol, 2 M in THF) was heated at 70° C. for 24 h. The reaction was quenched with EtOAc and washed with brine, dried (Na2SO4), and evaporated. Final purification by flash chromatography (hexane-EtOAc 25:1) afforded,406 mg of the title compound. MS m/z 339.3 (M++1).

Workup

  1. customThe reaction was quenched with EtOAc
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customFinal purification by flash chromatography (hexane-EtOAc 25:1)
  6. customafforded

Sources & evidence

ORD record
ord-46696f11a5414a8e89f9e15abb7d42f6
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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