p-Toluenesulfonic acid → [Rac]-2-[1-methyl-3-oxo-3-(4-trifluoromethyl-phenyl)-(z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester

HRID 479177Notes

Reaction equation

HRID 479177 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([NH2:31])[CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)[CH3:2].[F:33][C:34]([F:48])([F:47])[C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:46])[CH2:42][C:43](=O)[CH3:44])=[CH:37][CH:36]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([NH:31]/[C:43](/[CH3:44])=[CH:42]\[C:41](=[O:46])[C:38]1[CH:39]=[CH:40][C:35]([C:34]([F:33])([F:47])[F:48])=[CH:36][CH:37]=1)[CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 166409101-(4-(Trifluoromethyl)phenyl)butane-1,3-dioneHCID 69556623[Rac]-2-amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester

Product 1

HCID 70034562[Rac]-2-[1-methyl-3-oxo-3-(4-trifluoromethyl-phenyl)-(z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In analogy to the procedure described in example 105 a], [rac]-2-amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester was reacted with 1-(4-trifluoromethyl-phenyl)-butane-1,3-dione in toluene in the presence of a catalytic amount of p-toluene sulfonic acid at reflux to yield [rac]-2-[1-methyl-3-oxo-3-(4-trifluoromethyl-phenyl)-(Z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 105 b] to yield [rac]-2-[1-methyl-3-oxo-3-(4-trifluoromethyl-phenyl)-(Z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid as light yellow solid.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-b3011858a39741c992980e703419045a
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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