2-(4-(Methoxycarbonyl)phenyl)acetic acid → (E)-4-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl ester

HRID 1609310Notes

Reaction equation

HRID 1609310 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1.[CH:15]1([C:19]2[N:20]=[C:21](/[CH:24]=[CH:25]/[C:26]3[CH:27]=[C:28]([NH2:32])[CH:29]=[CH:30][CH:31]=3)[S:22][CH:23]=2)[CH2:18][CH2:17][CH2:16]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26](/[CH:25]=[CH:24]/[C:21]3[S:22][CH:23]=[C:19]([CH:15]4[CH2:18][CH2:17][CH2:16]4)[N:20]=3)[CH:27]=2)=[O:13])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 107978792-(4-(Methoxycarbonyl)phenyl)acetic acidHCID 15136086(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 67807759(E)-4-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl esterYield 95.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution composed of 1.0 g of 4-carboxymethyl benzoic acid methyl ester, 1.3 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine, 1.0 g of N-ethyl-N-(dimethylaminopropyl) carbodiimide, 2.4 g of 4-dimethylaminopyridine and 75 ml of methylene chloride at 0° C. After 16 hr. the reaction mixture was washed with 75 ml of water, dried (MgSO4) and the solvents removed by rotary evaporation. The residual materials were recrystallized with ethyl acetate to yield 2.1 g of (E)-4-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl ester; m.p. 163°-164° C.

Workup

  1. washthe reaction mixture was washed with 75 ml of water
  2. dry with materialdried (MgSO4)
  3. customthe solvents removed by rotary evaporation
  4. customThe residual materials were recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-86f5505afb1b4f599e929b10d82f8d13
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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