Isopropanol → HCID 58416774, compound

HRID 2069051Notes

Reaction equation

HRID 2069051 reaction equation
C[Li].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([CH2:17][C:18]([O:20]CC)=O)[CH:14]=[CH:13][N:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH:23](O)(C)C>C1COCC1>[O:20]=[C:18]([CH3:23])[CH2:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:4])([CH3:5])[CH3:6])[CH:16]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 53419364(2-Boc-amino-pyridin-4-yl)-acetic acid ethyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 58416774HCID 58416774, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyllithium (1.6 M in diethyl ether, 17.4 mL, 27.9 mmol) was added dropwise over 12 min to a stirred solution of ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)acetate (45) (1.56 g, 5.58 mmol) in THF (140 mL) under nitrogen at −78° C. After 3 hr isopropanol (5.0 mL) was added and the reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the combined organic extracts were washed with brine then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 80 g, 0-80% EtOAc in isohexane, gradient elution) to afford the title compound (46) (300 mg, 21%) as a white solid: m/z 251.0 (M+H)+ (ES+).

Workup

  1. customthe reaction mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialthen dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 80 g, 0-80% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-c688d56a6bd74bff906ba2460210e288
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

Loading…