Hydrochloric Acid → 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[({(2S)-1-[(4-methylphenyl)sulfonyl]piperidinyl}carbonyl)amino]propanoic acid

HRID 1869789Notes

Reaction equation

HRID 1869789 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH:20]([NH:25][C:26]([C@@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3[S:34]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])=[O:27])[C:21]([O:23]C)=[O:22])[CH:15]=2)[N:10]=1.[OH-].[Na+].O.Cl>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH:20]([NH:25][C:26]([C@@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3[S:34]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])=[O:27])[C:21]([OH:23])=[O:22])[CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68592952methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[({(2S)-1-[(4-methylphenyl)sulfonyl]piperidinyl}carbonyl)amino]propanoate

Product 1

HCID 685946963-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[({(2S)-1-[(4-methylphenyl)sulfonyl]piperidinyl}carbonyl)amino]propanoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 455 mg of methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[({(2S)-1-[(4-methylphenyl)sulfonyl]piperidinyl}carbonyl)amino]propanoate 46 in CH3OH (5 ml) are added 0.8 ml of 1 N NaOH and 1 ml of water. The solution is stirred at RT overnight, and 1 N HCl (0.8 ml) is added to obtain a weakly acidic pH. Methanol is then evaporated, and the solid obtained is filtered, washed with water and dried to give 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[({(2S)-1-[(4-methylphenyl)sulfonyl]piperidinyl}carbonyl)amino]propanoic acid 90.

Workup

  1. customto obtain a weakly acidic pH
  2. customMethanol is then evaporated
  3. customthe solid obtained
  4. filtrationis filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-fbc6bf3658b94033bff44305f5fd43e5
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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