Sodium Hydroxide → HCID 177807, compound

HRID 1742291Notes

Reaction equation

HRID 1742291 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]3[CH2:26][C:27]([O:29]C)=[O:28])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]3[CH2:26][C:27]([OH:29])=[O:28])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54162176HCID 54162176, compound

Product 1

HCID 177807HCID 177807, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(methoxycarbonylmethyl)piperidine (trans isomer) (210 mg) and 1N sodium hydroxide solution (0.573 ml) in methanol (2.0 ml) was heated to reflux for 2 hours. Methanol was evaporated in vacuo and water (20 ml) was added to the residue. The solution was acidified with 1N hydrochloric acid and extracted with methylene chloride (10 ml×2). The combined extracts were washed with brine (10 ml), dried over sodium sulfate and evaporated in vacuo. The crude crystals were recrystallized from a mixture of ethyl acetate and diethyl ether to give colorless crystals of (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(carboxymethyl)piperidine (trans isomer) (152.7 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customMethanol was evaporated in vacuo and water (20 ml)
  4. additionwas added to the residue
  5. extractionextracted with methylene chloride (10 ml×2)
  6. washThe combined extracts were washed with brine (10 ml)
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe crude crystals were recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-50f88bd202b5470b8b529e0b996618cd
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

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