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

HRID 1789863Notes

Reaction equation

HRID 1789863 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([CH2:7][C:8]1[C:9]([CH3:22])=[N:10][C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:12][CH:13]=1)=[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])[CH2:7][C:8]1[C:9]([CH3:22])=[N:10][C:11]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[CH:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 544728422-(6-Tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 543213072-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-yl)-propionic acid ethyl esterYield 87%

Procedure

TEA (0.556 mL, 3.99 mmol) was added to a solution of 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (1.23 g, 3.84 mmol) in thioacetic acid (10 mL) at 0 ° C. under argon. The mixture was stirred at room temperature for 64 h. EtOAc was added and the solution was washed with Na2CO3 and brine, dried and concentrated under reduced pressure. Flash chromatography (toluene/EtOAc, 5:1→1:1) gave 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-yl)-propionic acid ethyl ester (1.33 g, 87%).

Workup

  1. washthe solution was washed with Na2CO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d5d0fa9d6d04d2bbd3af2e94c61d5df
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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