Hydrochloric Acid → HCID 178456503, compound

HRID 248082Notes

Reaction equation

HRID 248082 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+].Cl>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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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 72%

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 (0.49 g, 1.07 mmol) in ethanol (10 mL) and treat with a solution of potassium hydroxide (0.072 g, 1.29 mmol) in water (10 mL). Stir for 3 hours, then dilute with water (200 mL) and acidify with 10% hydrochloric acid. Extract into chloroform (2×400 mL), then ether (400 mL) and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound as a white solid (0.33 g, 72%); [α]d 20 =+81° (C=0.069, DMSO).

Workup

  1. extractionExtract into chloroform (2×400 mL)
  2. dry with materialether (400 mL) and dry (MgSO4)
  3. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-2321ccff7101484bb3460d98e17caeb6
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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