Acetic Acid → HCID 58505812, compound

HRID 1917612Notes

Reaction equation

HRID 1917612 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C:3]([C:5]1[C:6]([CH3:32])=[C:7]([C:17]([N:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])=[O:18])[N:8]2[C:13]=1[CH:12]=[C:11]([CH:14]([CH3:16])[CH3:15])[CH:10]=[CH:9]2)=[O:4].[OH-].[Na+].CC(O)=O>O1CCOCC1.O>[CH3:34][C:2]([CH3:1])([CH3:33])[C:3]([C:5]1[C:6]([CH3:32])=[C:7]([C:17]([N:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:18])[N:8]2[C:13]=1[CH:12]=[C:11]([CH:14]([CH3:16])[CH3:15])[CH:10]=[CH:9]2)=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 66988966HCID 66988966, compound

Product 1

HCID 58505812HCID 58505812, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of methyl N-{[1-(2,2-dimethylpropanoyl)-2-methyl-7-(propan-2-yl)indolizin-3-yl]carbonyl}-N-phenyl-beta-alaninate (60 mg, 0.13 mmol) in 1,4-dioxane (5 mL) and water (1 mL) is added 10M aqueous NaOH (50 μL). The mixture is stirred at 23° C. for 2 h then acidified with HOAc, diluted water (5 mL), extracted with CH2Cl2, dried with MgSO4, filtered, and concentrated in vacuo to afford the title compound (42 mg, 72%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-377c3d56961f4673b06aa9fbfb72cad8
Source dataset
uspto-grants-2013_12
Patent number
US08618300B2

Reaction notes

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