HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetic Acid → 3-[3'-(3-Heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid

HRID 250863
Notes
Print preview

Reaction equation

HRID 250863 reaction equation
[OH-].[Na+].[CH3:3][N:4]([C:17]1[CH:18]=[C:19]([C:23]2C=CC(CCC(OCC)=O)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1C=C[CH:14]=[CH:13][CH:12]=1)=[O:6].O.[C:37]([OH:40])(=[O:39])[CH3:38].O1[CH2:45][CH2:44][CH2:43][CH2:42]1.[CH3:46]O>>[CH2:8]([NH:7][C:5](=[O:6])[N:4]([C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[CH:25][C:45]([CH2:46][CH2:38][C:37]([OH:40])=[O:39])=[CH:44][C:43]=2[CH3:42])[CH:20]=[CH:21][CH:22]=1)[CH3:3])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67272529Ethyl 3-{3'-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate

Product 1

HCID 117185193-[3'-(3-Heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid
Yield 55%

Procedure

100 mg (2.5 mmol, 3.2 eq) of sodium hydroxide are added to a solution of 348 mg (0.78 mmol, 1 eq) of ethyl 3-{3′-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate in 6 ml of a tetrahydrofuran/methanol mixture (8/2). The reaction mixture is stirred at room temperature for 12 hours. The reaction medium is hydrolyzed with water, acidified with acetic acid solution and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate). 180 mg of 3-[3′-(3-heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid are obtained in the form of a tacky solid. Yield=55%

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-6f40237e50844070b072f73b0b73b058
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863332B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes