Hydrochloric Acid → HCID 59038393, compound

HRID 1058446Notes

Reaction equation

HRID 1058446 reaction equation
[OH-:1].[Na+].C[O:4][C:5](=[O:36])/[C:6](/[NH:15][C:16](=[O:35])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]/[CH:24]=[C:25](/O)\[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:19][C:18]=1[Cl:34])=[CH:7]/[C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[CH3:14].Cl>O>[Cl:34][C:18]1[CH:19]=[C:20]([CH:23]([OH:1])/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH:21]=[CH:22][C:17]=1[C:16]([NH:15]/[C:6](=[CH:7]\[C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[CH3:14])/[C:5]([OH:4])=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86586332HCID 86586332, compound

Product 1

HCID 59038393HCID 59038393, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous 1N solution of sodium hydroxide (0.55 mL, 0.55 mmol) was added to a suspension of rac.-(Z)-2-[[2-chloro-4-[(E)-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester (Example 231; 90 mg, 0.175 mmol) in water (3 mL). The reaction mixture was stirred at room temperature for 5 h and then acidified with 1N hydrochloric acid solution (0.55 mL). The mixture was stirred for 30 min, then the solid was filtered off, washed with water, dried and evaporated. The crude acid was purified by reverse phase HPLC and lyophilized to give rac.-(Z)-2-[[2-chloro-4-[(E)-1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid (43 mg, 51% yield) as a colorless solid.

Workup

  1. stirringThe mixture was stirred for 30 min
  2. filtrationthe solid was filtered off
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe crude acid was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-540477d56f194cf187d6eb143a9e5766
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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