Water → (7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one

HRID 2364757ノート

反応式

HRID 2364757 の反応式
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1.[C:20]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:20])[C:7](=[O:12])[C@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 86668256(7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one

生成物 1

HCID 86668257(7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one収率 85%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

(7S)-2-Chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one 41e (2.80 g, 10 mmol) was dissolved in 50 mL of acetone followed by the addition of methyl p-toluenesulfonate (2.80 g, 15 mmol) and potassium carbonate (2.76 g, 20 mmol) successively, stirred for 12 hours. The resulting solution was added with 50 mL of water and extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure, The resulting residue was purified by silica gel column chromatography with elution system B to obtain the title compound (7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one 41f (2.50 g, yield: 85.0%) as a white solid.

後処理

  1. extractionextracted with ethyl acetate (100 mL×3)
  2. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system B

出典と根拠

ORDレコード
ord-f026b4c79c0a497e9a78e0a8a9591c4c
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

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