Trimethylsilyldiazomethane → HCID 118676283, compound

HRID 523044Notes

Reaction equation

HRID 523044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14]3[C:15](=[O:23])[O:16][C:17]([CH3:22])([C:19]([OH:21])=[O:20])[CH2:18][C:13]=3[N:12]=[CH:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:24][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[CH3:24][O:20][C:19]([C:17]1([CH3:22])[O:16][C:15](=[O:23])[C:14]2[N:10]([C:4]3[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[CH:3]=3)[CH:11]=[N:12][C:13]=2[CH2:18]1)=[O:21]

Participants

4

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 118676292HCID 118676292, compound

Product 1

HCID 118676283HCID 118676283, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To 50 mg (0.15 mmol) of 44 in 2 mL of a 1:1 CH2Cl2/MeOH is added 0.07 mL (0.14 mmol) of 2 M trimethylsilyl diazomethane in hexanes. After stirring for 1 h another 0.07 mL (0.14 mmol) of 2M trimethylsilyl diazomethane is added. The mixture is stirred for 1 h, concentrated, dissolved in 50 mL of EtOAc, and washed with twice with 20 mL of H2O and once with 20 mL of brine. The organic phase is dried with MgSO4, filtered, and concentrated to give 21 mg (0.06 mmol) of 45.

Workup

  1. additionis added
  2. concentrationconcentrated
  3. dissolutiondissolved in 50 mL of EtOAc
  4. washwashed with twice with 20 mL of H2O
  5. dry with materialThe organic phase is dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0082e0bd0d474ac19cd0607b09414e94
Source dataset
uspto-grants-2016_05
Patent number
US09334285B2

Reaction notes

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