Hydrochloric Acid → 3-{4-[3-(3-Bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoylamino}propionic acid

HRID 49551Notes

Reaction equation

HRID 49551 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]=3)=[CH:28][CH:27]=2)[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=2)=[O:17])=[CH:10][CH:9]=1.[OH-].[Li+].Cl>C1COCC1.O>[Br:25][C:21]1[CH:20]=[C:19]([NH:18][C:16](=[O:17])[N:15]([CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:39])=[O:2])=[O:38])=[CH:13][CH:12]=2)[C:26]2[CH:27]=[CH:28][C:29]([C:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]=3)=[CH:30][CH:31]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 67483870HCID 67483870, compound

Product 1

HCID 101208673-{4-[3-(3-Bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoylamino}propionic acidYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[3-(3-Bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoylamino}propionic acid methyl ester (0.64 g, 1.08 mmol) was dissolved in THF (10 ml) and lithium hydroxide (0.043 g, 1.08 mmol) in water (1 ml) was added and the resulting mixture was stirred at room temperature for 16 hours. More lithium hydroxide (0.043 g, 1.08 mmol) in water (1 ml) was added and, after 4 hours, 1N hydrochloric acid (2.2 ml) was added. The mixture was concentrated in vacuo and the residue was triturated with water, filtered and dried in vacuo at 40° C. to afford 0.378 g (61%) of 3-{4-[3-(3-bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoylamino}propionic acid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was triturated with water
  3. filtrationfiltered
  4. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-246957b59fd44eb9a670730f9625d210
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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