Methanol → HCID 20084378, compound

HRID 327575

Reaction equation

HRID 327575 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 20084378HCID 20084378, compound

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-d1088dbe04f84eb8b13c01945267d780
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Linked notes

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