Acetone → (3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}propionic acid phenyl ester

HRID 423273Notes

Reaction equation

HRID 423273 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][N:9]([CH3:42])[C:10]([C:12]1[CH:13]=[C:14]([CH2:37][CH2:38]C(O)=O)[CH:15]=[CH:16][C:17]=1[NH:18][C:19]([C:21]1[C:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20])=[O:11].CCN=C=NCCCN(C)C.Cl.C[C:56](C)=[O:57]>CN(C)C1C=CN=CC=1>[C:1]1([O:7][C:56](=[O:57])[CH:37]([C:14]2[CH:15]=[CH:16][C:17]([NH:18][C:19]([C:21]3[C:22]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:29][CH:28]=4)=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:20])=[C:12]([C:10](=[O:11])[N:9]([CH3:8])[CH3:42])[CH:13]=2)[CH3:38])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 996PhenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666765733-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}propionic acid

Product 1

HCID 86761487(3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}propionic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Dimethylaminopyridine (30 mg), phenol (23 mg), and 3-{3-dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}propionic acid (100 mg) were dissolved in acetone (1 mL). After addition of WSC hydrochloride (50 mg), the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated, and purified by column chromatography on silica gel (ethyl acetate:hexane=1:1, v/v) to give the title compound (Compound 1-1) (0.088 g) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-656b8bfeb36a4ad8b326d7ac2b7b38b2
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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