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Water → 3-methoxycarbonylpropanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

HRID 2380669
Notes
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Reaction equation

HRID 2380669 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7](O)=[O:8].[CH2:11]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:19][CH:18]=1)[CH2:12][CH2:13][CH3:14].CCN(C(C)C)C(C)C.O>C(OCC)(=O)C>[CH2:11]([N:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:19][CH:18]=1)[C:7](=[O:8])[CH2:6][CH2:5][C:4]([O:3][CH3:2])=[O:10])[CH2:12][CH2:13][CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 153383534'-Butylaminomethyl-2-cyanobiphenylHCID 86605420Succinic acid methylester chloride

Product 1

HCID 540165583-methoxycarbonylpropanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent
2×

Procedure

A solution of 5.1 g (34 mmol) of succinic acid monomethyl ester monochloride in 20 ml of ethyl acetate is added dropwise, while cooling with ice, to a solution of 6.0 g (22.7 mmol) of N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amine and 13 ml of Hunig base in 100 ml of ethyl acetate. The reaction mixture is stirred at from 0° to 5° for 1 hour and then 30 ml of water are added. The organic phase is washed in succession with 30 ml of 2N hydrochloric acid, water and saturated potassium hydrogen carbonate solution and is dried. Evaporation of the solvent yields crude 3-methoxycarbonylpropanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide in the form of an oil that has an Rf value of 0.32 [toluene/methanol (19:1)].

Workup

  1. washThe organic phase is washed in succession with 30 ml of 2N hydrochloric acid, water and saturated potassium hydrogen carbonate solution
  2. customis dried
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-598954d691d24dcf91a97aeaefafca1d
Source dataset
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05369110

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes