HCID 67374343, compound → HCID 86608787, compound

HRID 1677613Notes

Reaction equation

HRID 1677613 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7](=[CH2:11])[C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[C:12]([OH:15])(=[S:14])[CH3:13].C(O)(C)C>>[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([CH2:11][S:14][C:12](=[O:15])[CH3:13])[C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 67374343HCID 67374343, compoundHCID 178459215HCID 178459215, compound

Product 1

HCID 86608787HCID 86608787, compound

Procedure

A solution of 2-(piperidin-4-yl)prop-2-enoic acid (0.30 g, 1.64 mmol) in 6 mL of 1:1 thioacetic acid/isopropanol was stirred for 24 hours. The reaction mixture was concentrated in vacuo to afford the crude product, 2-(piperidin-4-yl)-3-(acetylthio)propanoic acid. The product was dissolved in 2 mL of water, cooled to 0° C., degassed with nitrogen, and 2 mL of ammonium hydroxide was added. The reaction mixture was stirred for 1 hour, concentrated in vacuo and the residue was dissolved in 10% HCl and purified by preparative HPLC to afford 73 mg of pure 2-(piperidin-4-yl)-3-mercaptopropanoic acid, as a trifluoroacetic acid salt, NMR (D2O) 1.30-1.43 (m, 2), 1.70-1.90 (m, 3), 2.32-2.42 (m, 1), 2.50-2.60 (m, 1), 2.63-2.72 (m, 1), 2.79-2.90 (m, 2), 3.22-3.34 (m, 2) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5c01c0fab1854fe482ee7d9d4a1d3841
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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