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

HRID 2364755ノート

反応式

HRID 2364755 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.ClCCl>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

6

反応物 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 68728583methyl (2S)-2-(cyclopentylamino)butanoate

生成物 1

HCID 86668255methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate収率 44.3%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

反応条件

温度
85 °C

実験手順

Methyl (2S)-2-(cyclopentylamino)butanoate 41c (17.36 g, 93.69 mmol) was dissolved in 180 mL of cyclohexane followed by the addition of sodium bicarbonate (31.48 g, 0.37 mol) and 2,4-dichloro-5-nitro-pyrimidine (21.81 g, 0.11 mol) successively. The reaction solution was heated to 85° C. and stirred for 2 hours. The resulting solution was cooled down to room temperature, added with 300 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 the title compound methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate 41d (14.24 g, yield: 44.3%) as a yellow solid.

後処理

  1. temperatureThe resulting solution 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

出典と根拠

ORDレコード
ord-7e44164c2db14dd5ab6b84a574757d33
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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