Hydrochloric Acid → HCID 58629918, compound

HRID 1391819Notes

Reaction equation

HRID 1391819 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C@H:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([O:31]CC)=[O:30])=[C:23]([CH3:34])[CH:22]=3)[CH2:16][O:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].O.[OH-].[Na+].Cl>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C@H:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:23]([CH3:34])[CH:22]=3)[CH2:16][O:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58629900HCID 58629900, compound

Product 1

HCID 58629918HCID 58629918, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [(4-{[(1S)-1-[6-(4-cyanophenyl)-2-pyridinyl]-2-(ethyloxy)ethyl]oxy}-2-methylphenyl)oxy]acetate (0.886 g) was dissolved in THF (8.8 mL). Water (8.8 mL) and aq 2M NaOH (1.8 mL) were added and the mixture stirred at ambient temperature for 30 mins. The reaction mixture was acidified to pH 1 by the addition of aq 2M HCl and extracted with EtOAc (2×10 mL). The organic extracts were washed with brine (20 mL), dried (Na2SO4) and evaporated to give the title compound as a white foam (729 mg).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe organic extracts were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-fb976be071444f52a0d7450fc56b4c0b
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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