Triethylamine → HCID 53756755, compound

HRID 1789918Notes

Reaction equation

HRID 1789918 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:36])[C:12]([CH:14]([C:22]1[CH:23]=[N:24][C:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:26][CH:27]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:13])[CH3:9].C(OCC)(=O)C.[C:43]([OH:46])(=[S:45])[CH3:44]>>[CH2:8]([O:10][C:11](=[O:36])[CH:12]([CH2:13][S:45][C:43](=[O:46])[CH3:44])[CH:14]([C:22]1[CH:23]=[N:24][C:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:26][CH:27]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:9]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54436772HCID 54436772, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 53756755HCID 53756755, compoundYield 65%

Conditions

Temperature
45 °C

Procedure

Triethylamine (0.096 g, 0.95 mmol) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-acrylic acid ethyl ester (0.34 g, 0.86 mmol) in thioacetic acid (3.5 mL) at 0° C. under argon. The mixture was heated at 45° C. for 24 h. Ethyl acetate was added and the organic phase was washed with aqueous saturated sodium bicarbonate and brine and dried. After filtration and evaporation in vacuo the crude product was purified by flash chromatography (CH2Cl2/ethyl acetate, 1:0→100:5) to give 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-4-phenyl-butyric acid ethyl ester (0.264 g, 65%).

Workup

  1. washthe organic phase was washed with aqueous saturated sodium bicarbonate and brine
  2. customdried
  3. filtrationAfter filtration and evaporation in vacuo the crude product
  4. customwas purified by flash chromatography (CH2Cl2/ethyl acetate, 1:0→100:5)

Sources & evidence

ORD record
ord-1f4ca76aef404411a3eb336929b17465
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…