Triethylamine → HCID 54210448, compound

HRID 1789808Notes

Reaction equation

HRID 1789808 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH2:7][C:8]1[CH:9]=[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].C(N(CC)CC)C.[C:30]([OH:33])(=[S:32])[CH3:31]>>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([CH2:6][S:32][C:30](=[O:33])[CH3:31])[CH2:7][C:8]1[CH:9]=[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)[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 54494317Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylateHCID 178418634HCID 178418634, compound

Product 1

HCID 54210448HCID 54210448, compoundYield 61%

Procedure

2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.49 g, 1.60 mmol) and triethylamine (0.17 g, 1.64 mmol) were added to thioacetic acid (3 mL) at 0° C. The mixture was stirred at room temperature for 6 h. The mixture was poured onto ice-water and extracted with CH2Cl2. The organic phase was washed with saturated NaHCO3 and dried. The crude product was purified by flash chromatography (MeOH/CH2Cl2, 2.5:100) to give 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-propionic acid ethyl ester (0.36 g, 61%).

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed with saturated NaHCO3
  4. customdried
  5. customThe crude product was purified by flash chromatography (MeOH/CH2Cl2, 2.5:100)

Sources & evidence

ORD record
ord-96d8d198c68c43a1930af17b5b4a14c6
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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