Lithium hydroxide, monohydrate → (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid

HRID 1058451Notes

Reaction equation

HRID 1058451 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:37])/[C:7](/[NH:16][C:17](=[O:36])[C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)=[O:25])=[CH:20][C:19]=1[Cl:35])=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1>O.O1CCCC1.CO.O>[Br:15][C:12]1[CH:13]=[CH:14][C:9](/[CH:8]=[C:7](\[NH:16][C:17](=[O:36])[C:18]2[CH:23]=[CH:22][C:21]([C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=3)=[O:25])=[CH:20][C:19]=2[Cl:35])/[C:6]([OH:37])=[O:5])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59038409(Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester

Product 1

HCID 59038339(Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acidYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of lithium hydroxide monohydrate (10.6 mg, 0.25 mmol) in water (1 mL) was added to a solution of (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (Example 224; 69 mg, 0.13 mmol) in tetrahydrofuran/methanol/water (3:1:1; 1.5 ml). The mixture was stirred for 4 h at room temperature and then acidified. The product was filtered off and purified by HPLC (Waters system) to give (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid (33 mg, 49% yield).

Workup

  1. filtrationThe product was filtered off
  2. custompurified by HPLC (Waters system)

Sources & evidence

ORD record
ord-4c06110b627e45a0bd7fdf31d41acf64
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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