Sodium Hydroxide → 4-[4-(4-(2-[(2R)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-ethyl}-phenylamino)-piperidine-1-carbonyl]-benzoic acid

HRID 1281614Notes

Reaction equation

HRID 1281614 reaction equation
[OH:1][C@H:2]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:33]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:31]=[CH:30][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[OH:1][C@H:2]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])[CH:33]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:31]=[CH:30][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 69985586Methyl 4-{[4-(4-{2-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]ethyl}anilino)-1-piperidinyl]carbonyl}benzoate

Product 1

HCID 699855594-[4-(4-(2-[(2R)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-ethyl}-phenylamino)-piperidine-1-carbonyl]-benzoic acidYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-{[4-(4-{2-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]ethyl}anilino)-1-piperidinyl]carbonyl}benzoate (0.127 g, 0.208 mmol) was dissolved in methanol (12 mL) and 1N sodium hydroxide (0.416 mL) added. The reaction was stirred at reflux for 24 hours. A further portion of 1N sodium hydroxide (0.1 mL) was added and the reaction stirred at reflux for a further 24 hours. The solvent was removed in vacuo. The residue was extracted with ethyl acetate and the solvent removed in vacuo. The residue was extracted with methanol, filtered through Celite and the solvent removed in vacuo to furnish the title compound (0.032 g, 0.054 mmol).

Workup

  1. temperatureat reflux for 24 hours
  2. stirringthe reaction stirred
  3. temperatureat reflux for a further 24 hours
  4. customThe solvent was removed in vacuo
  5. extractionThe residue was extracted with ethyl acetate
  6. customthe solvent removed in vacuo
  7. extractionThe residue was extracted with methanol
  8. filtrationfiltered through Celite
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-bc6acd4d5fe743dfaab104c842504837
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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