Sodium Hydroxide → HCID 117631196, compound

HRID 1481981Notes

Reaction equation

HRID 1481981 reaction equation
[CH2:1]([O:4][C:5]1([CH3:36])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=[C:15]3[CH:14]=[C:13]([CH3:25])[C:12]=2[C@H:26]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:27]([O:29][CH3:30])=[O:28])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[OH-].[Na+]>CO>[CH2:1]([O:4][C:5]1([CH3:36])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=[C:15]3[CH:14]=[C:13]([CH3:25])[C:12]=2[C@H:26]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:27]([O:29][CH3:30])=[O:28])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117635649HCID 117635649, compound

Product 1

HCID 117631196HCID 117631196, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(S)-Ethyl 5-(4-(allyloxy)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate (450 mg, 0.923 mmol, 1 equiv) was dissolved in MeOH (9 mL). To this solution was added 1 N NaOH (1.02 mL, 1.015 mmol, 1.1 equiv). The reaction was stirred at 60° C. for 2 h. Upon cooling to ambient temperature, the reaction was concentrated in vacuo. The residue was then azeotroped with toluene to give a pale brown solid (S)-5-(4-(allyloxy)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid (400 mg, 92% yield) which was used as is for further reactions. LCMS (ESI, M+1): 474.35.

Workup

  1. temperatureUpon cooling to ambient temperature
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe residue was then azeotroped with toluene

Sources & evidence

ORD record
ord-c5e145036ef5415c9b84ac6addca3b12
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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