Potassium Bicarbonate → 3-[(2-Chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester

HRID 2111347ノート

反応式

HRID 2111347 の反応式
[C:1]([O:5][C:6](=[O:13])[CH2:7][CH2:8][NH:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1.C(=O)(O)[O-].[K+]>O.C(OCC)C>[C:1]([O:5][C:6](=[O:13])[CH2:7][CH2:8][N:9]([C:17]1[C:18]([N+:22]([O-:24])=[O:23])=[CH:19][N:20]=[C:15]([Cl:14])[N:16]=1)[CH:10]([CH3:11])[CH3:12])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 42656868tert-Butyl 3-[(propan-2-yl)amino]propanoate

生成物 1

HCID 866234133-[(2-Chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester収率 92.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

A solution of 0.935 g (0.005 mole) of 3-isopropylamino-propanoic acid tert-butyl ester in 20 mL of water was added dropwise to a solution of 0.97 g (0.005 mole) of 2,4-dichloro-5-nitro-pyrimidine in 20 mL of ethyl ether. At 0 degrees, 1.0 g (0.010 mole) of potassium bicarbonate was added. The mixture was stirred at ambient temperature for 3 hours. The layers were then separated, and the aqueous layer extracted twice with 30 mL of ether. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-80:20) gave 1.6 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester (IV-43).

後処理

  1. customThe layers were then separated
  2. extractionthe aqueous layer extracted twice with 30 mL of ether
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (100:0-80:20)

出典と根拠

ORDレコード
ord-03806cc9011a4081bc698f2b84574e07
出典データセット
uspto-grants-2009_04
特許番号
US07517873B2

反応ノート

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