3-Fluorophenylalanine → HCID 52936160, compound

HRID 2401324Notes

Reaction equation

HRID 2401324 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[C:3]([OH:5])=[O:4].C([O-])([O-])=O.[K+].[K+].Cl[C:21]1[N:22]([CH2:37][CH2:38][CH3:39])[C:23](=[O:36])[C:24]2[NH:25][C:26]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[N:27][C:28]=2[N:29]=1.[Cl-].[NH4+]>O>[CH:30]1([C:26]2[NH:25][C:24]3[C:23](=[O:36])[N:22]([CH2:37][CH2:38][CH3:39])[C:21]([NH:1][CH:2]([CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=4)[C:3]([OH:5])=[O:4])=[N:29][C:28]=3[N:27]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 99763-FluorophenylalanineHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 67192333HCID 67192333, compound

Product 1

HCID 52936160HCID 52936160, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-Amino-3-(3-fluoro-phenyl)-propionic acid (112 mg, 0.612 mmol) and K2CO3 (140 mg, 1.02 mmol) in water (5 ml) was added 2-Chloro-8-cyclohexyl-1-propyl-1,7-dihydro-purin-6-one (150 mg, 0.51 mmol). The reaction mixture was stirred at refluxing temperature for overnight. Aqueous ammonium chloride was added to the reaction mixture. The solid obtained was filtered and dried. The crude product was purified by preparative HPLC to obtain 4 mg (˜2%) of pure product as pink solid.

Workup

  1. temperatureat refluxing temperature for overnight
  2. customThe solid obtained
  3. filtrationwas filtered
  4. customdried
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-9afcd95c824744f49d0dcf8989a17998
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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