Triethylamine → 2-Acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-pyridin-4-yl)-propionic acid ethyl ester

HRID 1789799Notes

Reaction equation

HRID 1789799 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]=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:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 544852162-(2-Tert-butoxycarbonylamino-pyridin-4-ylmethyl)-acrylic acid ethyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 867601162-Acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-pyridin-4-yl)-propionic acid ethyl esterYield 100%

Procedure

A solution of 2-(2-tert-butoxycarbonylamino-pyridin-4-ylmethyl)-acrylic acid ethyl ester (0.48 g, 1.57 mmol) and triethylamine (0.17 g, 1.64 mmol) was added to thioacetic acid (3 mL) at 0° C. under nitrogen. The mixture was stirred at room temperature for 4 h. The mixture was poured onto ice-water and extracted with CH2Cl2. The organic phase was washed with saturated NaHCO3 (aq) and dried. The crude product was purified by flash chromatography (2.5% MeOH in CH2Cl2) to give 2-acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-pyridin-4-yl)-propionic acid ethyl ester (0.60 g, 100%).

Workup

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

Sources & evidence

ORD record
ord-c5acf6150bfe4f35aa8cbad2307fd951
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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