Hydrochloric Acid → HCID 11180513, compound

HRID 900371Notes

Reaction equation

HRID 900371 reaction equation
C([O:3][C:4](=[O:44])[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]3[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[O:33][C:32]=3[CH2:40][CH2:41][CH2:42][CH3:43])=[CH:26][CH:25]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:6])C.[OH-].[Na+].Cl>C(O)C>[CH2:40]([C:32]1[O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:31]=1[CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:10]2[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:8]([NH:7][C:5](=[O:6])[C:4]([OH:44])=[O:3])[CH:9]=2)=[CH:25][CH:26]=1)[CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59696185HCID 59696185, compound

Product 1

HCID 11180513HCID 11180513, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid ethyl ester (120 mg, 0.204 mmol) in ethanol (3 mL) was treated with aq 1 N NaOH (0.3 mL, 1.5 equiv., 0.306 mmol) and stirred at room temperature. After stirring 1 h, the solution was acidified to pH<4 with 10% HCl, concentrated and purified by prep thin layer chromatography (10% methanol in dichloromethane) afforded N-[4′-(2-Butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid (32 mg, 28%).

Workup

  1. stirringAfter stirring 1 h
  2. concentrationconcentrated
  3. custompurified by prep thin layer chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6e56f74656f240459bbd2384548ccb8b
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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