Ethyl Acetate → 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-butyric acid ethyl ester

HRID 1789855Notes

Reaction equation

HRID 1789855 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([CH:7]([C:9]1[CH:10]=[N:11][C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:13][CH:14]=1)[CH3:8])=[CH2:6])[CH3:2].CCOC(C)=O.[C:30]([OH:33])(=[S:32])[CH3:31]>>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([CH2:6][S:32][C:30](=[O:33])[CH3:31])[CH:7]([C:9]1[CH:10]=[N:11][C:12]([NH:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[CH:13][CH:14]=1)[CH3:8])[CH3:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 696502442-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-acrylic acid ethyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 867601172-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-butyric acid ethyl esterYield 91%

Conditions

Temperature
45 °C

Procedure

TEA (0.076 mL, 0.542 mmol) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-acrylic acid ethyl ester (158 mg, 0.493 mmol) in thioacetic acid (2 mL) at 0° C. under argon. The mixture was stirred at 45° C. over night. EtOAc was added and the solution was washed with NaHCO3 and brine, dried and concentrated under reduced pressure. Flash chromatography (toluene/EtOAc, 5:1→1:1) gave slightly unpure 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-butyric acid ethyl ester (178 mg, 91%).

Workup

  1. washthe solution was washed with NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-761d9ebecdbe44d99dedfd4f28298023
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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