Toluene → HCID 58674326, compound

HRID 1994144Notes

Reaction equation

HRID 1994144 reaction equation
C(OC([C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[C:17]([CH2:21][CH2:22][C:23]([OH:25])=O)[CH:18]=[CH:19][CH:20]=2)[CH:11]=[CH:10][N:9]=1)=O)(C)(C)C.Cl[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33](OC(C)(C)C)=O)[CH:28]=1.C[Si](C=[N+:45]=[N-])(C)C.CCCCCC.[C:53]1([CH3:59])[CH:58]=CC=C[CH:54]=1>CO>[NH2:45][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[C:17]([CH2:21][CH2:22][C:23]([NH:30][C:29]3[CH:33]=[CH:31][CH:32]=[C:27]([C:53]([CH3:59])([CH3:58])[CH3:54])[CH:28]=3)=[O:25])[CH:18]=[CH:19][CH:20]=2)[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 11806045tert-Butyl 4-chloropicolinateHCID 58674576HCID 58674576, compound

Product 1

HCID 58674326HCID 58674326, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(3-{[2-(tert-butoxycarbonyl)pyridin-4-yl]oxy}phenyl)propanoic acid (prepared from tert-butyl 4-chloropyridine-2-carboxylate using the procedure described for Example 8, Step 1, 1.13 g, 32.9 mmol), in MeOH (15 mL) and toluene (15 mL) was added a 2.0M solution of trimethylsilyldiazomethane in hexane (3.29 mL, 65.8 mmol) dropwise. The mixture was stirred for 2 h. The solvents were evaporated and the residue was dissolved in EtOAc, washed with sat. NaHCO3 solution and brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography to yield the title compound (779 mg, 66.2%). LCMS: (FA) ES+ 358.3 (M+1), 302.2 (-tBu).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2c51a4a5146d4921b30de65901cdbb1d
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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