Hydrochloric Acid → HCID 59038452, compound

HRID 1058445Notes

Reaction equation

HRID 1058445 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:39])/[C:6](/[NH:18][C:19](=[O:38])[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([OH:36])/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[CH:22][C:21]=1[Cl:37])=[CH:7]/[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2.Cl>O>[Cl:37][C:21]1[CH:22]=[C:23]([CH:26]([OH:36])/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)[CH:24]=[CH:25][C:20]=1[C:19]([NH:18]/[C:6](=[CH:7]\[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)/[C:5]([OH:39])=[O:4])=[O:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59038473HCID 59038473, compound

Product 1

HCID 59038452HCID 59038452, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous 1N solution of sodium hydroxide (0.6 mL, 0.6 mmol) was added to a suspension of rac.-(Z)-2-[[2-chloro-4-[(E)-1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (Example 230; 95 mg, 0.184 mmol) in water (2 mL). The reaction mixture was stirred at room temperature for 16 h and then acidified with 1N hydrochloric acid solution (0.6 mL). The mixture was stirred for 1 h, then the solid was filtered off, washed with water, dried and 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-(quinolin-3-yl)propenoic acid (57 mg, 62% yield) as a colorless solid.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationthe solid was filtered off
  3. washwashed with water
  4. customdried
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-62651bb733594a468ff2efbf2d662eb6
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

Loading…