Trimethylsilyldiazomethane → HCID 46240008, compound

HRID 553681Notes

Reaction equation

HRID 553681 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:13][C:14]1[C:15]([CH3:35])=[N:16][O:17][C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:12])[CH3:9].[CH3:36][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[CH3:36][O:33][C:32](=[O:34])[CH2:31][C:28]1[CH:27]=[CH:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([C:18]3[O:17][N:16]=[C:15]([CH3:35])[C:14]=3[NH:13][C:11]([O:10][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH3:9])=[O:12])=[CH:20][CH:21]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 46239909HCID 46239909, compound

Product 1

HCID 46240008HCID 46240008, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To (4′-{4-[1-(2-chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-acetic acid (0.050 g, 0.1 mmol) in benzene (17 mL) and methanol (2 mL) was added (trimethylsilyl)diazomethane (2M in hexanes; 0.1 mL, 0.2 mmol), and the reaction was stirred at room temperature for 5 minutes. Additional (trimethylsilyl)diazomethane (2M in hexanes; 0.25 mL, 0.5 mmol) was added, and the reaction was stirred until no starting material was seen by analytical LCMS. The mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed twice with water and once with brine, and then dried and concentrated. The residue was purified by silica gel chromatography (0-80% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringthe reaction was stirred until no starting material
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed twice with water and once with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-81747ee7c5034936be7b3bf1f415baa1
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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