Lithium Hydroxide → 3-(4-Cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(4-(quinolin-7-yl)phenyl)propanoic acid

HRID 1525855Notes

Reaction equation

HRID 1525855 reaction equation
[CH:1]1([N:4]2[CH2:9][C:8]3([CH2:14][CH2:13][N:12]([CH:15]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:36]=[C:35]6[C:30]([CH:31]=[CH:32][CH:33]=[N:34]6)=[CH:29][CH:28]=5)=[CH:23][CH:22]=4)[CH2:16][C:17]([O:19]C)=[O:18])[CH2:11][CH2:10]3)[O:7][CH2:6][C:5]2=[O:37])[CH2:3][CH2:2]1.[Li+].[OH-]>C(O)C>[CH:1]1([N:4]2[CH2:9][C:8]3([CH2:10][CH2:11][N:12]([CH:15]([C:21]4[CH:22]=[CH:23][C:24]([C:27]5[CH:36]=[C:35]6[C:30]([CH:31]=[CH:32][CH:33]=[N:34]6)=[CH:29][CH:28]=5)=[CH:25][CH:26]=4)[CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:14]3)[O:7][CH2:6][C:5]2=[O:37])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71271322HCID 71271322, compound

Product 1

HCID 712707553-(4-Cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(4-(quinolin-7-yl)phenyl)propanoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(4-(quinolin-7-yl)phenyl)propanoate (0.238 mmol) in ethanol (1 mL) was treated with LiOH (0.476 mmol) and stirred at room temperature for four days. The reaction mixture was concentrated in vacuo and the residue purified by reverse phase HPLC (15-50% acetonitrile/water with 0.1% NH4OH) to afford the title compound as a white solid (72%). MS(ES)+ m/e 486.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by reverse phase HPLC (15-50% acetonitrile/water with 0.1% NH4OH)

Sources & evidence

ORD record
ord-77be47c9654141b1ad957e8af7ea0f65
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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