Hydrochloric Acid → HCID 10121328, compound

HRID 1634829Notes

Reaction equation

HRID 1634829 reaction equation
[OH:1][C@H:2]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:32]=1)[CH2:3][NH:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([C:26]([O:28]CC)=[O:27])[CH:23]=[N:22]3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1.[OH-].[Na+].Cl>CO>[OH:1][C@H:2]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:32]=1)[CH2:3][NH:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[N:22]3)=[CH:17][CH:16]=2)(=[O:13])=[O:14])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10304551HCID 10304551, compound

Product 1

HCID 10121328HCID 10121328, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 1-{4-[(4-{[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)-amino]phenyl}ethyl)amino]methyl}piperidin-1-yl)sulfonyl]-phenyl}-1H-pyrazole-4-carboxylate (0.118 g, 0.18 mmol) and 0.8 mL of 1N NaOH in 10 mL methanol was heated at reflux overnight. On cooling the reaction was neutralized with 0.8 mL of 1N HCl. The reaction mixture was concentrated in vacuo and triturated with H2O. The solids were filtered and dried (high vacuum) to give 0.095 g of the title compound as an off white solid.

Workup

  1. temperatureat reflux overnight
  2. temperatureOn cooling the reaction
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customtriturated with H2O
  5. filtrationThe solids were filtered
  6. customdried (high vacuum)

Sources & evidence

ORD record
ord-433e483372224038b914cc19b3215b7f
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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