Trimethylsilyldiazomethane → HCID 66631998, compound

HRID 931832Notes

Reaction equation

HRID 931832 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])=[C:10]([CH3:21])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:22][OH:23])=[N:7]2.[CH3:24][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[Br:1][C:2]1[C:11]([C@H:12]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[C:13]([O:15][CH3:24])=[O:14])=[C:10]([CH3:21])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:22][OH:23])=[N:7]2

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane5×HCID 66631828HCID 66631828, compound

Product 1

HCID 66631998HCID 66631998, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-(5-bromo-2-(hydroxymethyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetic acid (3.6 g, 9.4 mmol) in anhydrous dichloromethane and methanol (1:1, 20 mL) was added (trimethylsilyl)diazomethane (2 M in hexanes, 5.17 mL, 10.34 mmol) and the reaction was stirred at room temperature for three hours. An additional 2 mL of (trimethylsilyl)diazomethane was added and stirred for 2 hours, followed by an additional 1 mL of (trimethylsilyl)diazomethane for 1 hour, then 1 mL of (trimethylsilyl)diazomethane added and let go overnight. An additional 3.5 mL of (trimethylsilyl)diazomethane were added and stirred for 1 hour. The reaction was quenched with 30 mL of acetic acid and then stirred 15 minutes. The reaction was concentrated under reduced pressure and then absorbed onto silica. The crude reaction was purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a yellow foam (2.37 g). LCMS-ESI+ (m/z): [M+H]+ calcd C18H23BrNO4: 396.07. found: 396.71.

Workup

  1. stirringstirred for 2 hours
  2. waitlet go overnight
  3. stirringstirred for 1 hour
  4. customThe reaction was quenched with 30 mL of acetic acid
  5. stirringstirred 15 minutes
  6. concentrationThe reaction was concentrated under reduced pressure
  7. customabsorbed onto silica
  8. customThe crude reaction
  9. customwas purified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e9f5f6700a5f48f59e162b8837fb70ef
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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