Hydrochloric Acid → HCID 22482219, compound

HRID 2181704Notes

Reaction equation

HRID 2181704 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1.O.[Li+].[OH-].Cl>C1COCC1.CCOC(C)=O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[C:13]=[CH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 10309800HCID 10309800, compound

Product 1

HCID 22482219HCID 22482219, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.105 g (0.257 mmol) of the compound of Example 9 is dissolved in 25 ml of 90% THF:10% water. 10 equivalents of LiOH are added. The reaction is refluxed for 3 hours, 200 ml of EtOAc are added, acidified by concentrated HCl and the solution is washed with 2×100 ml of water and 1×100 ml of brine. Organic layer dried over MgSO4, and concentrated. The residue is purified on a silica gel column with 95% EtOAc:5% MeOH to yield 30 mg of the product as a light yellow powder.

Workup

  1. temperatureThe reaction is refluxed for 3 hours
  2. washthe solution is washed with 2×100 ml of water and 1×100 ml of brine
  3. dry with materialOrganic layer dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified on a silica gel column with 95% EtOAc

Sources & evidence

ORD record
ord-f0eb6d50f7c0441395bb7dcaade9b039
Source dataset
uspto-grants-2005_05
Patent number
US06894057B2

Reaction notes

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