Hydrochloric Acid → (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-ethyl-4-methylthiazole-5-yl)propenoic acid

HRID 1058450Notes

Reaction equation

HRID 1058450 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:38])/[C:7](/[NH:17][C:18](=[O:37])[C:19]1[CH:24]=[CH:23][C:22]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])=[CH:21][C:20]=1[Cl:36])=[CH:8]/[C:9]1[S:13][C:12]([CH2:14][CH3:15])=[N:11][C:10]=1[CH3:16].Cl>O.O1CCCC1.CO>[Cl:36][C:20]1[CH:21]=[C:22]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])[CH:23]=[CH:24][C:19]=1[C:18]([NH:17]/[C:7](=[CH:8]\[C:9]1[S:13][C:12]([CH2:14][CH3:15])=[N:11][C:10]=1[CH3:16])/[C:6]([OH:38])=[O:5])=[O:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59038457(Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-ethyl-4-methylthiazole-5-yl)propenoic acid methyl ester

Product 1

HCID 59038338(Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-ethyl-4-methylthiazole-5-yl)propenoic acidYield 105%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (100 mg, 2.4 mmol) in water (3 mL) was added to a solution of (Z)-3-(2-ethyl-4-methylthiazole-5-yl)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2-methylbenzoyl]amino]propenoic acid methyl ester (Example 216; 120 mg, 0.2 mmol) in tetrahydrofuran/methanol (3:1; 12 mL) and the reaction was allowed to stir at room temperature overnight. Water (50 mL) and 1N hydrochloric acid solution (3 mL) were added and the mixture was extracted with ethyl acetate (2×50 mL). The ethyl acetate layers were concentrated and purified by HPLC to give (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-ethyl-4-methylthiazole-5-yl)propenoic acid (105 mg, 90% yield) as a colorless solid, mp>200° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. concentrationThe ethyl acetate layers were concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-756751a4cbde4e64b81274163ce6b8e2
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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