Hydrochloric Acid → (RS)-3-[4-[1-(4-tert-Butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic Acid

HRID 967642Notes

Reaction equation

HRID 967642 reaction equation
C([O:3][C:4](=[O:43])[CH:5]([OH:42])[CH2:6][NH:7][C:8](=[O:41])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>C(O)C>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH:15]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:32][CH:31]=2)=[O:28])[C:12]2[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][CH:5]([OH:42])[C:4]([OH:43])=[O:3])=[O:41])=[CH:10][CH:11]=2)=[CH:21][CH:20]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674831433-{4-[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

Product 1

HCID 22311113(RS)-3-[4-[1-(4-tert-Butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic AcidYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-{4-[1-(4-tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester was stirred in absolute ethanol (20 mL) and 1 M sodium hydroxide (6 mL) was added. Stirring was continued for 17 hours and the solution was acidified with aqueous hydrochloric acid. The solvent was decanted and the remaining oil was dissolved in acetonitrile (20 mL) by heating. Water (20 mL) was added dropwise under vigorous stirring and the mixture was allowed to cool to room temperature. The precipitate was filtered off, washed with water and dried to afford 0.51 g (43%) of the title compound as a solid.

Workup

  1. customThe solvent was decanted
  2. dissolutionthe remaining oil was dissolved in acetonitrile (20 mL)
  3. temperatureby heating
  4. additionWater (20 mL) was added dropwise
  5. stirringunder vigorous stirring
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d5b4cbd0943243a7b44db2374e93aab5
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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