Lithium hydroxide, monohydrate → (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid

HRID 1058447Notes

Reaction equation

HRID 1058447 reaction equation
C[O:2][C:3](=[O:35])/[C:4](/[NH:14][C:15](=[O:34])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[O:23])=[CH:18][C:17]=1[Cl:33])=[CH:5]/[C:6]1[S:10][CH:9]=[N:8][C:7]=1[CH:11]([CH3:13])[CH3:12].O.[OH-].[Li+]>CO.O1CCCC1.O>[Cl:33][C:17]1[CH:18]=[C:19]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[O:23])[CH:20]=[CH:21][C:16]=1[C:15]([NH:14]/[C:4](=[CH:5]\[C:6]1[S:10][CH:9]=[N:8][C:7]=1[CH:11]([CH3:13])[CH3:12])/[C:3]([OH:35])=[O:2])=[O:34]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 59038382(Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid methyl ester

Product 1

HCID 59038377(Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acidYield 58%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid methyl ester (Example 232; 75 mg, 0.146 mmol) and lithium hydroxide monohydrate (24 mg, 0.572 mmol) in methanol/tetrahydrofuran/water (2:2:1; 1.25 mL) was stirred at room temperature for 90 min. A further potion of lithium hydroxide monohydrate (6 mg, 0.143 mmol) was added and the reaction mixture was allowed to stir at room temperature for 65 h. After the reaction mixture was evaporated to dryness, water was added, followed by 1N hydrochloric acid solution (0.72 mL). The resulting colorless precipitate was filtered off, then was purified by reverse phase HPLC and lyophilized to afford (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid (42 mg, 58% yield) as a colorless powder.

Workup

  1. stirringto stir at room temperature for 65 h
  2. customAfter the reaction mixture was evaporated to dryness, water
  3. additionwas added
  4. filtrationThe resulting colorless precipitate was filtered off
  5. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-030fb0ceec6d44c39a7d56b2fc2b5770
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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