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

HRID 396083Notes

Reaction equation

HRID 396083 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-319e70f0f0a44f81b556f8e754e5b9da
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

Loading…