Sodium Hydroxide → HCID 58281318, compound

HRID 552320Notes

Reaction equation

HRID 552320 reaction equation
C([O:3][C:4](=[O:43])[C@@H:5]([NH:13][C:14](=[O:42])[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]3[N:29]([C:33]4[C:38]([CH3:39])=[CH:37][C:36]([Br:40])=[CH:35][C:34]=4[CH3:41])[CH:30]=[C:31]([CH3:32])[C:23]=23)[CH2:18][CH2:17]1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+].OS([O-])(=O)=O.[K+]>CCO>[Br:40][C:36]1[CH:37]=[C:38]([CH3:39])[C:33]([N:29]2[C:24]3=[N:25][C:26]([CH3:28])=[CH:27][C:22]([N:19]4[CH2:20][CH2:21][CH:16]([CH2:15][C:14]([NH:13][C@@H:5]([CH2:6][C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)[C:4]([OH:43])=[O:3])=[O:42])[CH2:17][CH2:18]4)=[C:23]3[C:31]([CH3:32])=[CH:30]2)=[C:34]([CH3:41])[CH:35]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 11650376HCID 11650376, compound

Product 1

HCID 58281318HCID 58281318, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-2-(2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetylamino)-3-phenyl-propionic acid ethyl ester (140 mg), 4 M NaOH (1 mL) and EtOH (2 mL) was stirred at room temperature for 24 hours. 1 M KHSO4 (10 mL) was added into the reaction mixture and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: CHCl3:MeOH=9/1) to obtain the title compound (35 mg) as an amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: CHCl3:MeOH=9/1)

Sources & evidence

ORD record
ord-3ac2a605a55b45fca21285cef2fd9c8e
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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