Hydrochloric Acid → HCID 58505676, compound

HRID 1917599Notes

Reaction equation

HRID 1917599 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]=[CH:23][N:22]=4)[CH:16]=[CH:17]3)=[C:12]([C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C:11]=2[CH2:33][C:34]([CH3:41])([CH3:40])[C:35]([O:37]CC)=[O:36])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO>[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]=[CH:23][N:22]=4)[CH:16]=[CH:17]3)=[C:12]([C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C:11]=2[CH2:33][C:34]([CH3:41])([CH3:40])[C:35]([OH:37])=[O:36])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58505688HCID 58505688, compound

Product 1

HCID 58505676HCID 58505676, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-(pyridin-2-ylmethoxy)indolizin-2-yl}-2,2-dimethylpropanoate (98 mg, 0.17 mmol) in THF (1 mL), MeOH (1 mL), and 6M aqueous NaOH (0.75 mL) is heated at 50° C. for 3 h then cooled to 23° C. and acidified to pH=1 with concentrated aqueous HCl. The mixture is partitioned between CH2Cl2 and brine then the organics are collected and dried with MgSO4, filtered, and concentrated in vacuo to afford the title compound (80 mg, 86%).

Workup

  1. customThe mixture is partitioned between CH2Cl2 and brine
  2. customthe organics are collected
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf688a3594f240ae8ae38d85d6d083c2
Source dataset
uspto-grants-2013_12
Patent number
US08618300B2

Reaction notes

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