Hydrochloric Acid → (R)-3-{4-[3-(3-Bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid

HRID 967636Notes

Reaction equation

HRID 967636 reaction equation
C([O:3][C:4](=[O:41])[C@H:5]([OH:40])[CH2:6][NH:7][C:8](=[O:39])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=2)=[O:18])=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>C(O)C>[Br:26][C:22]1[CH:21]=[C:20]([NH:19][C:17](=[O:18])[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:8]([NH:7][CH2:6][C@@H:5]([OH:40])[C:4]([OH:41])=[O:3])=[O:39])=[CH:14][CH:13]=2)[C:27]2[CH:32]=[CH:31][C:30]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67483100(R)-3-{4-[3-(3-bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

Product 1

HCID 10282059(R)-3-{4-[3-(3-Bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acidYield 39.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{4-[3-(3-Bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester (100 mg) was dissolved in ethanol (10 mL), 1 N sodium hydroxide (480 μL) was added and the resulting mixture was stirred at room temperature for 1 hour. 1 N Hydrochloric acid (480 μL) was added and the mixture was concentrated in vacuo. The residue was suspended in water (50 mL) and filtered to afford 38 mg of the title compound.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. filtrationfiltered

Sources & evidence

ORD record
ord-84982c59482849738edb3e2caac69fdb
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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