Hydrochloric Acid → (4-Purin-9-yl-phenyl)-acetic acid

HRID 1661034Notes

Reaction equation

HRID 1661034 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:20]=[N:19][C:18]3[C:13]2=[N:14][CH:15]=[N:16][C:17]=3Cl)=[CH:8][CH:7]=1)C.[Li+].[OH-].C1COCC1.Cl>CO.[Pd]>[N:16]1[CH:17]=[C:18]2[C:13]([N:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:22])=[O:3])=[CH:11][CH:10]=3)[CH:20]=[N:19]2)=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86625827[4-(6-Chloro-purin-9-yl)phenyl]-acetic acid ethyl ester

Product 1

HCID 67021576(4-Purin-9-yl-phenyl)-acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [4-(6-chloro-purin-9-yl)phenyl]-acetic acid ethyl ester (182 mg, 0.60 mmol) and Pd/C (10%) in MeOH containing 5% ammonia (15 mL) is stirred for 22 h at rt and under hydrogen (2 bar). The reaction mixture is filtered through a pad of celite and concentrated. The residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 95:5), followed by trituration in Et2O to afford a mixture of (4-purin-9-yl-phenyl)-acetic acid methyl and ethyl ester. This mixture is treated with a 2 N aqueous solution of LiOH (0.5 mL), and THF (1 mL) for 3 h at 50° C. The reaction mixture is allowed to cool to rt and then acidified by addition of 0.5 N HCl aqueous solution. The resulting precipitate is collected by vacuum filtration to provide the title compound as a white solid: ES-MS: 255.1 [M+H]+; tR=1.93 min (System 1).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 95:5)
  4. customto afford
  5. temperatureto cool to rt
  6. filtrationThe resulting precipitate is collected by vacuum filtration

Sources & evidence

ORD record
ord-bf398b3596ac4d12a41493c8affa307a
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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