Hydrochloric Acid → 3-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}propionic acid

HRID 49548Notes

Reaction equation

HRID 49548 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][CH2:5][NH:6][C:7](=[O:40])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)[C:16]([NH:18][C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH3:20])=[O:17])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@@H: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:41])=[O:2])=[O:40])=[CH:13][CH:12]=2)[C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)=[CH:30][CH:29]=2)[CH3:20])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674838893-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]-1-(4-cyclohexylphenyl)ureidomethyl]benzoyl-amino}propionic acid methyl ester

Product 1

HCID 101879053-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoyl-amino}propionic acid methyl ester (1.1 g, 1.9 mmol) was dissolved in methanol (10 ml) and 1N aqueous sodium hydroxide (5.7 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Then 1N hydrochloric acid was added and the solvent was removed by rotary evaporation in vacuo. The residue was re-dissolved in ethyl acetate and diethyl ether and crystallised using sonication. Concentration in vacuo followed by re-suspension in a aqueous hydrochloric acid and sinication for 30 min afforded after filtration, washing with water and drying in vacuo 0.55 g (51%) of the title compound as a solid.

Workup

  1. customthe solvent was removed by rotary evaporation in vacuo
  2. dissolutionThe residue was re-dissolved in ethyl acetate
  3. customdiethyl ether and crystallised
  4. customsonication
  5. concentrationConcentration in vacuo
  6. waitfollowed by re-suspension in a aqueous hydrochloric acid and sinication for 30 min
  7. customafforded
  8. filtrationafter filtration
  9. washwashing with water
  10. dry with materialdrying in vacuo 0.55 g (51%) of the title compound as a solid

Sources & evidence

ORD record
ord-152dddcab7874b5084519bba6b107877
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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