Tetrahydrofuran → HCID 20084370, compound

HRID 327579Notes

Reaction equation

HRID 327579 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]3[S:23][CH:24]=[C:25]([CH:27]4[CH2:30][CH2:29][CH2:28]4)[N:26]=3)[CH:15]=2)=[O:12])=[C:6]([O:31][CH3:32])[CH:5]=1.O1CCCC1.O.[OH-].[Li+]>CO>[CH:27]1([C:25]2[N:26]=[C:22](/[CH:21]=[CH:20]/[C:16]3[CH:15]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:33])=[O:2])=[CH:5][C:6]=4[O:31][CH3:32])[CH:19]=[CH:18][CH:17]=3)[S:23][CH:24]=2)[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67808922HCID 67808922, compound

Product 1

HCID 20084370HCID 20084370, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.57 g of (E)-4-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]-3-methoxybenzoic acid methyl ester, 25 ml of tetrahydrofuran, 8 ml of methanol and 0.28 g of lithium hydroxide monohydrate was stored at 25° C. for 20 hr. The solvents were removed by rotary evaporation and the residual materials solubilized in 50 ml of water. Acetic acid was added and the precipitate of (E)-4-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]-3-methoxybenzoic acid was isolated by filtration, m.p. 242°-243° C. after trituration with hot acetonitrile.

Workup

  1. customThe solvents were removed by rotary evaporation
  2. additionAcetic acid was added

Sources & evidence

ORD record
ord-7f725504bc164a7ea143fb0239527b8c
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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