Sodium Hydroxide → HCID 57554776, compound

HRID 1511885Notes

Reaction equation

HRID 1511885 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([C@H:22]4[CH2:33][CH2:32][C:24]5([NH:28][C:27](=O)[N:26](C)[C:25]5=[O:31])[CH2:23]4)=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>O1CCOCC1>[NH2:28][C:24]1([C:25]([NH:26][CH3:27])=[O:31])[CH2:32][CH2:33][C@H:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[N:12]=[C:11]([C:8]4[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=4)[O:15][N:14]=3)=[CH:17][CH:18]=2)[CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57554627HCID 57554627, compound

Product 1

HCID 57554776HCID 57554776, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(7S)-7-(4-(5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)-3-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (0.052 g, 0.117 mmol) was taken up in dioxane (1.0 ml). To this was added sodium hydroxide (1.0 ml, 2.000 mmol) as 2M solution. The resulting suspension was heated to 120° C. for about 70 hours, during which more sodium hydroxide solution was added to push the hydrolysis to completion. Heating was stopped and the reaction mixture was concentrated in vacuo. The resulting material was brought up in 1-2 mL DMSO and filtered. The filtrate was purified on a Prep HPLC system using 30-100% acetonitrile in 50 mM NH4OAc buffer at 21 mL/min to yield (3S)-1-amino-3-(4-(5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)-N-methylcyclopentanecarboxamide (0.017 g, 0.041 mmol) as off-white solid.

Workup

  1. additionwas added
  2. customthe hydrolysis to completion
  3. temperatureHeating
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. filtrationfiltered
  6. customThe filtrate was purified on a Prep HPLC system

Sources & evidence

ORD record
ord-a869ff0465e64fac8c9777c9ef4ee4c3
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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