Acetic Acid → HCID 58505643, compound

HRID 1917603Notes

Reaction equation

HRID 1917603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[N:22]=4)[CH:16]=[CH:17]3)=[C:12]([C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:11]=2[CH2:35][C:36]([CH3:43])([CH3:42])[C:37]([O:39]CC)=[O:38])=[O:9])=[CH:4][CH:3]=1.CC(O)=O>C1COCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[N:22]=4)[CH:16]=[CH:17]3)=[C:12]([C:29](=[O:34])[C:30]([CH3:32])([CH3:33])[CH3:31])[C:11]=2[CH2:35][C:36]([CH3:43])([CH3:42])[C:37]([OH:39])=[O:38])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 58505712HCID 58505712, compound

Product 1

HCID 58505643HCID 58505643, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-[(6-methoxypyridin-2-yl)methoxy]indolizin-2-yl}-2,2-dimethylpropanoate (20 mg, 0.033 mmol) in THF (2.0 mL) and 10M aqueous NaOH (1.5 mL) is heated at 45° C. for 1.5 h. The mixture is then acidified with HOAc, concentrated in vacuo, and partitioned between EtOAc and water. The organics are collected, dried with MgSO4, filtered, and concentrated in vacuo to give the title compound (19 mg, quant).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. customThe organics are collected
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19cf73d45fd94019a2344bf8dca9d781
Source dataset
uspto-grants-2013_12
Patent number
US08618300B2

Reaction notes

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