Hydrochloric Acid → 4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid

HRID 49546Notes

Reaction equation

HRID 49546 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[C:12]([NH:14][C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH3:16])=[O:13])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C(O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C@@H:15]([NH:14][C:12](=[O:13])[N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:36])=[O:2])=[CH:9][CH:8]=2)[C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[CH:26][CH:25]=2)[CH3:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674831604-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester

Product 1

HCID 674838354-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester (35.0 g, 69.3 mmol) was dissolved in ethanol (400 ml). 4 N aqueous sodium hydroxide (100 ml) was added and the clear solution was stirred at room temperature for 3 hours. The solution was neutralised with 4 N hydrochloric acid (100 ml), and placed upon an ice bath to initiate crystallization. The crystals were collected, washed extensively with water, and dried in vacuo over night. Yield: 34.25 g (100%).

Workup

  1. customplaced upon an ice bath
  2. customcrystallization
  3. customThe crystals were collected
  4. washwashed extensively with water
  5. customdried in vacuo over night

Sources & evidence

ORD record
ord-7af1638ce1584aa88bd007f7e2b7b78e
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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