Hydrochloric Acid → 3-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)phenyl]-2-hydroxypropionic acid

HRID 30728Notes

Reaction equation

HRID 30728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([OH:31])[C:27]([O:29]C)=[O:28])=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH:26]([OH:31])[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=2)=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69205606HCID 69205606, compound

Product 1

HCID 692070433-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)phenyl]-2-hydroxypropionic acidYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)phenyl]-2-hydroxypropionate (1.34 g), a 2N aqueous sodium hydroxide solution (10 ml) and methanol (20 ml) was stirred at room temperature for 1 hr. The reaction mixture was poured into a 1N aqueous hydrochloric acid solution (100 ml). The precipitated solids were collected by filtration, washed with water and dried to give 3-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)phenyl]-2-hydroxypropionic acid (800 mg, 62%) as colorless crystals.

Workup

  1. filtrationThe precipitated solids were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-19c19f11770644038a011d1b9c17cf2d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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