Triethylamine → 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-3-phenyl-propionic acid ethyl ester

HRID 1789914Notes

Reaction equation

HRID 1789914 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:35])[C:12]([CH:14]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:13])[CH3:9].C(OCC)(=O)C.[C:42]([OH:45])(=[S:44])[CH3:43]>>[CH2:8]([O:10][C:11](=[O:35])[CH:12]([CH2:13][S:44][C:42](=[O:45])[CH3:43])[CH:14]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:9]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 537546282-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 539704052-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-3-phenyl-propionic acid ethyl esterYield 73%

Conditions

Temperature
45 °C

Procedure

Triethylamine (0.105 g, 1.04 mmol) was added to a solution of 2-[(6tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl ester (0.36 g, 0.94 mmol) in thioacetic acid (4 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 (toluene/ethyl acetate, 1:0→5:1) to give 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (0.314 g, 73%).

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 (toluene/ethyl acetate, 1:0→5:1)

Sources & evidence

ORD record
ord-7ff9aa4d50ed477f91ea9ca5941afd61
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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