Potassium Hydroxide → HCID 178456503, compound

HRID 248085Notes

Reaction equation

HRID 248085 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[C:9]([CH:14]([CH3:29])[CH2:15][C:16]3[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])=[CH:18][CH:17]=3)[NH:8][C:7]=2[N:6]([CH2:30][CH2:31][CH3:32])[C:5]1=[O:33])[CH2:2][CH3:3].[OH-].[K+]>C(O)C.O>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[C:9]([CH:14]([CH3:29])[CH2:15][C:16]3[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)[NH:8][C:7]=2[N:6]([CH2:30][CH2:31][CH3:32])[C:5]1=[O:33])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178456507(+)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid, ethyl ester

Product 1

HCID 178456503HCID 178456503, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Dissolve (-)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid, ethyl ester (0.62 g, 1.36 mmol) in ethanol (15 mL) and treat with a solution of potassium hydroxide (0.091 g, 1.63 mmol) in water (15 mL). Stir for 3 hours, add water (200 mL) and wash with ethyl ether (300 mL). Acidify the aqueous phase with 10% hydrochloric acid and extract into chloroform (4×150 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (0.47 g, 81%); [α]d 20 =-79.1° (C=0.537, DMSO).

Workup

  1. washwash with ethyl ether (300 mL)
  2. extractionextract into chloroform (4×150 mL)
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-135da97fb3444ae4b09205e5c434360a
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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