Methanol → (E)-2-[3-[3-[2-[4-(Cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid

HRID 1609337Notes

Reaction equation

HRID 1609337 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[C:24]2[S:25][CH:26]=[C:27]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[N:28]=2)[CH:17]=1)=[O:14])C.O1CCCCC1.CO.O.[OH-].[Li+]>O>[CH:29]1([C:27]2[N:28]=[C:24](/[CH:23]=[CH:22]/[C:18]3[CH:17]=[C:16]([NH:15][C:13](=[O:14])[CH2:12][CH2:11][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[C:4]([OH:33])=[O:3])[CH:21]=[CH:20][CH:19]=3)[S:25][CH:26]=2)[CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8894TetrahydropyranHCID 168937Lithium hydroxide, monohydrateHCID 67808810HCID 67808810, compound

Product 1

HCID 20084378(E)-2-[3-[3-[2-[4-(Cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution composed of 0.457 g of (E)-2-[3-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid ethyl ester, 25 ml of tetrahydropyran, 8 ml of methanol, 8 ml of water and 0.282 g of lithium hydroxide monohydrate was allowed to stand at room temperature for 20 hr. The solvents were removed by rotary evaporation and the residual materials were taken up in 30 ml of water. Addition of excess acetic acid caused the precipitation of 0.42 g of (E)-2-[3-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid; m.p. 238°-239° C.

Workup

  1. customThe solvents were removed by rotary evaporation
  2. additionAddition of excess acetic acid
  3. customthe precipitation of 0.42 g of (E)-2-[3-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid

Sources & evidence

ORD record
ord-e7b97b6304874cc88c6394717c5416ba
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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