Sodium Hydroxide → (R)-3-{4-[1-(4-Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic Acid

HRID 412428Notes

Reaction equation

HRID 412428 reaction equation
C([O:3][C:4](=[O:46])[C@H:5]([OH:45])[CH2:6][NH:7][C:8](=[O:44])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([O:42][CH3:43])[CH:33]=2)=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+]>C(O)C>[CH:22]1([C:19]2[CH:18]=[CH:17][C:16]([CH:15]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:35]=[C:34]([O:42][CH3:43])[CH:33]=3)=[O:30])[C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C@@H:5]([OH:45])[C:4]([OH:46])=[O:3])=[O:44])=[CH:10][CH:11]=3)=[CH:21][CH:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483036(R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

Product 1

HCID 67484722(R)-3-{4-[1-(4-Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{4-[1-(4-Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoyl-amino}-2-hydroxypropionic acid ethyl ester was dissolved in ethanol (15 mL) and sodium hydroxide (2 N, 2 mL) was added. The reaction mixture was stirred at room temperature for 60 min. Then ethanol was removed in vacuo, water (50 mL) was added and pH was adjusted with 4 N hydrochloric acid to acidic reaction. Filtration and washing with water (5×5 mL) and drying in vacuo afforded 460 mg of the title compound as a crystalline solid.

Workup

  1. customThen ethanol was removed in vacuo, water (50 mL)
  2. additionwas added
  3. custompH was adjusted with 4 N hydrochloric acid to acidic reaction
  4. filtrationFiltration
  5. washwashing with water (5×5 mL)
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-163600f6d19b4a83b76c1008c5b6e80f
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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