Sodium Hydroxide → (S)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid sodium salt

HRID 1481972Notes

Reaction equation

[CH2:1]([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)[CH2:2][CH:3]=[CH2:4].[OH-].[Na+:38]>CO>[Na+:38].[CH2:1]([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])=[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)[CH2:2][CH:3]=[CH2:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-ethyl 5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate (0.164 g, 0.328 mmol, 1 equiv) in MeOH (3.3 mL) was added 1 N NaOH (0.36 mL, 0.36 mmol, 1.1 equiv). After stirring 18 h, the reaction was heated to 60° C. for 2 h. Upon cooling to ambient temperature, the reaction was concentrated in vacuo. The residue was then concentrated in vacuo with toluene (×3) to remove residual MeOH to provide the product as a yellow solid (0.168 g, 100%). LCMS (ESI, M+1): 472.3.

Workup

temperatureUpon cooling to ambient temperature
concentrationthe reaction was concentrated in vacuo
concentrationThe residue was then concentrated in vacuo with toluene (×3)
customto remove residual MeOH

Sources & evidence

ORD record: ord-96fccc865aa74160b1d8167311a6401c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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