Dichloromethane → methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate

HRID 2364764노트

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HRID 2364764 반응식
[CH:1]([NH:4][C@@H:5]([CH2:10][CH3:11])[C:6]([O:8][CH3:9])=[O:7])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1.ClCCl>C1CCCCC1>[Cl:17][C:18]1[N:23]=[C:22]([N:4]([CH:1]([CH3:3])[CH3:2])[C@@H:5]([CH2:10][CH3:11])[C:6]([O:8][CH3:9])=[O:7])[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 86668259methyl (2S)-2-(isopropylamino)butanoate

생성물 1

HCID 86668260methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate수율 41.1%

시약·촉매·용매 1

HCID 8078Cyclohexane용매

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온도
85 °C

실험 절차

Methyl (2S)-2-(isopropylamino)butanoate 43a (10.75 g, 67.50 mmol) was dissolved in 180 mL of cyclohexane followed by the addition of sodium bicarbonate (22.68 g, 0.27 mol) and 2,4-dichloro-5-nitro-pyrimidine (15.71 g, 0.081 mol) successively, the reaction mixture was heated to 85° C. and stirred for 2.5 hours. The resulting mixture was cooled down to room temperature, added with 200 mL of dichloromethane, 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 methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 43b (8.78 g, yield: 41.1%) as a yellow solid.

후처리

  1. temperatureThe resulting mixture was cooled down to room temperature
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography with elution system B

출처 및 근거

ORD 기록
ord-a38e9e5b319048c5a82cfea3cc1496c9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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