Dichloromethane → 4-Tert-Butyl 1-methyl 2-((7-methyl-1H-indazol-5-yl)methyl)succinate

HRID 2099829Notes

Reaction equation

HRID 2099829 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH3:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2)[CH2:5][C:6]([OH:8])=[O:7].[C:21](OC(=N)C(Cl)(Cl)Cl)([CH3:24])([CH3:23])[CH3:22].B(F)(F)F.CCOCC.C(Cl)Cl>O1CCCC1>[CH3:19][C:17]1[CH:18]=[C:10]([CH2:9][CH:4]([CH2:5][C:6]([O:8][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:7])[C:3]([O:2][CH3:1])=[O:20])[CH:11]=[C:12]2[C:16]=1[NH:15][N:14]=[CH:13]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 184521154-methoxy-3-((7-methyl-1H-indazol-5-yl)methyl)-4-oxobutanoic acid

Product 1

HCID 577947204-Tert-Butyl 1-methyl 2-((7-methyl-1H-indazol-5-yl)methyl)succinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-3-((7-methyl-1H-indazol-5-yl)methyl)-4-oxobutanoic acid (0.9764 g, 3.54 mmol) and t-butyl-2,2,2-trichloroacetoimidate (3.78 mL, 21.22 mmol) in tetrahydrofuran (25 mL) was added 1M boron trifluoride etherate (0.2 mL) at room temperature. Heat generation was observed and the reaction was stirred for 3.5 h before passing it through a pad of silica gel. Evaporation of the filtrate gave a white solid. Methylene chloride (20 mL) was added and the resulting white solid was removed by filtration. The filtrate was concentrated and the final product was obtained via silica gel chromatography eluting with 0% to 50% ethyl acetate/hexane. (0.605 g, 52%) HPLC tR=1.51 min, MS(ESI)[M+H]+=332.77.

Workup

  1. temperatureHeat generation
  2. customEvaporation of the filtrate
  3. customgave a white solid
  4. customthe resulting white solid was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-aa6066628f6c40c8b75a75fca9f74d27
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

Loading…