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

HRID 2364663

반응식

HRID 2364663 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8078Cyclohexane용매

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ab0765c4c4ee474aa0f12a5b24397d9d
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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