Hydrochloric Acid → HCID 68819523, compound

HRID 736760Notes

Reaction equation

HRID 736760 reaction equation
C([O:3][C:4]([CH:6]1[CH:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([CH2:35][CH2:36][OH:37])[CH2:7]1)=[O:5])C.Cl>O1CCOCC1>[OH:37][CH2:36][CH2:35][N:8]1[CH2:9][CH2:10][CH:11]([NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68817820HCID 68817820, compound

Product 1

HCID 68819523HCID 68819523, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(2-hydroxy-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester (0.6 g, 1.14 mmol) in 1,4-dioxane (10 mL) was added concentrated HCl (10 mL). The reaction was heated to 60° C. for 19 h and the solvent was then removed in vacuo. The residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column eluting with an acetonitrile:water gradient to afford 1-(2-hydroxy-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid as an amorphous white solid (0.4 g, 71.4%). MS: 500 (M+H)+.

Workup

  1. customthe solvent was then removed in vacuo
  2. customThe residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column
  3. washeluting with an acetonitrile

Sources & evidence

ORD record
ord-c85b9be9b24a4abbbcac1f2b1cb13417
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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