Sodium Hydroxide → HCID 86587296, compound

HRID 1582046Notes

Reaction equation

HRID 1582046 reaction equation
ClC(Cl)(Cl)COC([N:7]1[C:19]2[CH2:18][N:17]([S:20]([CH2:23][CH:24]([CH:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])[CH2:31][CH2:30]3)[C:25](=[O:28])[NH:26][OH:27])(=[O:22])=[O:21])[CH2:16][CH2:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=O.[OH-].[Na+]>CO>[CH2:38]([O:37][C:35]([N:32]1[CH2:33][CH2:34][CH:29]([CH:24]([C:25](=[O:28])[NH:26][OH:27])[CH2:23][S:20]([N:17]2[CH2:16][CH2:15][C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:19]=3[CH2:18]2)(=[O:22])=[O:21])[CH2:30][CH2:31]1)=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10146857HCID 10146857, compound

Product 1

HCID 86587296HCID 86587296, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(1-Benzyloxycarbonyl-piperidin-4-yl)-2-hydroxycarbamoyl-ethane sulfonyl]-1,2,3,4-tetrahydro-β-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl ester (135 mg) and 0.1N sodium hydroxide (4.2 ml) in methanol were stirred at room temperature for 3.5 h. The methanol was removed under reduced pressure and the residue partitioned between dichloromethane (20 ml) and 5% citric acid solution (5 ml). The aqueous was extracted with 10% methanol in dichloromethane (2×20 ml) and the combined organics washed with water (2×30 ml) and evaporated tinder reduced pressure to give the title compound (82 mg, 80%) as a white solid.

Workup

  1. customThe methanol was removed under reduced pressure
  2. customthe residue partitioned between dichloromethane (20 ml) and 5% citric acid solution (5 ml)
  3. extractionThe aqueous was extracted with 10% methanol in dichloromethane (2×20 ml)
  4. washthe combined organics washed with water (2×30 ml)
  5. customevaporated

Sources & evidence

ORD record
ord-699bb808be274313b9346155d445f6a0
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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