Sodium Bicarbonate → (R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate

HRID 2364663

反応式

HRID 2364663 の反応式
[CH:1]1([NH:6][C@H:7]([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1>C1CCCCC1>[Cl:19][C:20]1[N:25]=[C:24]([N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C@H:7]([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57358664(R)-Methyl 2-(cyclopentylamino)butanoate

生成物 1

HCID 58405447(R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate収率 72.6%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

反応条件

温度
60 °C

実験手順

Methyl (2R)-2-(cyclopentylamino)butanoate 1k (2.50 g, 13.50 mmol) and sodium bicarbonate (4.54 g, 54 mmol) were dissolved in 100 mL of cyclohexane, stirred for 30 minutes followed by the addition of 2,4-dichloro-5-nitro-pyrimidine (2.88 g, 14.84 mmol), heated to 60° C. and stirred for another 12 hours. The reaction mixture was filtered, washed with dichloromethane (50 mL), and the filtrate was concentrated under reduced pressure, the resulting residue was recrystallized by 150 mL of the mixture solvent of ethyl acetate and n-hexane (V/V=1:4) to obtain the title compound methyl (2R)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-(1-cyclopentyl)amino]butanoate 1m (3.36 g, yield: 72.6%) as a light yellow solid.

後処理

  1. stirringstirred for another 12 hours
  2. filtrationThe reaction mixture was filtered
  3. washwashed with dichloromethane (50 mL)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was recrystallized by 150 mL of the mixture solvent of ethyl acetate and n-hexane (V/V=1:4)

出典と根拠

ORDレコード
ord-ab0765c4c4ee474aa0f12a5b24397d9d
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

関連ノート

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