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

HRID 412454Notes

Reaction equation

HRID 412454 reaction equation
COC(=O)[C:4]1[CH:9]=C[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](C2C=CC(Cl)=CC=2)C)=[O:13])=[CH:6][CH:5]=1.[OH-:37].[Na+].[ClH:39].[CH2:40]([OH:42])[CH3:41]>>[Cl:39][C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([C:6]2[C:7]([CH2:10][N:11]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]4[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)=[CH:26][CH:25]=3)[C:12]([NH2:14])=[O:13])=[C:41]([CH:9]=[CH:4][CH:5]=2)[C:40]([OH:37])=[O:42])[CH3:31])=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 674831604-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester

Product 1

HCID 867589653-[1(S)-(4-Chlorophenyl)ethyl]-1-(4-cyclohexylphenyl)ureidomethyl benzoic Acid

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 overnight. 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 overnight

Sources & evidence

ORD record
ord-6dd0af8ea8a940fe8b2c94cfac56e655
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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