Trimethylsilane → HCID 578300, compound

HRID 2175308Notes

Reaction equation

HRID 2175308 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14].[CH3:17][SiH](C)C>C(Cl)Cl.CO>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([O:15][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 70435TrimethylsilaneHCID 749491HCID 749491, compound

Product 1

HCID 578300HCID 578300, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((2,3-dimethylphenyl)amino)-4-oxobutanoic acid (0.5 g, 2.26 mmol) in DCM (9 mL) and MeOH (2 mL) at room temperature was added 2.0 M diazomethyl)trimethylsilane (1.36 mL, 2.71 mmol) dropwise. The reaction was stirred at room temperature for 30 min and quenched with a solution of 20% AcOH in DCM). The mixture was concentrated and purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound as a white solid (0.52 g, 98% yield). LCMS, [M+H]+=236.4.

Workup

  1. customquenched with a solution of 20% AcOH in DCM)
  2. concentrationThe mixture was concentrated
  3. custompurified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-aea55a74a1a740c3835f3c0bceb38978
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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