Chloroacetaldehyde → Ethyl 2-amino-1H-pyrrole-3-carboxylate

HRID 63774

反応式

HRID 63774 の反応式
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](=[NH:8])[NH2:7])[CH3:2].Cl[CH2:11][CH:12]=O>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:12]=[CH:11][NH:8][C:6]=1[NH2:7])=[O:9])[CH3:2]

参加物

4

反応物 2

HCID 33ChloroacetaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl ester

生成物 1

HCID 12111022Ethyl 2-amino-1H-pyrrole-3-carboxylate収率 31%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Carbamimidoyl-acetic acid ethyl ester (3.357 g, 25.8 mmol) was dissolved in AcOEt (20 mL). Chloroacetaldehyde (50% solution in water, 1.8 mL, 28.7 mmol) was added rapidly at room temperature. The solution stirred for 2 minutes until a precipitant formed. The solution was then brought to 65° C. for 0.5 h. The reaction mixture was then cooled and flash chromatographed with AcOEt. Product containing fractions were concentrated to give the desired material as a green solid. 0.68 g obtained, 31% yield. 1H NMR (400 MHz, CDCl3) δ 1.32 (t, J=7.2 Hz, 3H), 4.24 (q, J=7.0 Hz, 2H), 5.08 (brs, 2H), 6.10-6.13 (m, 1H), 6.25 (t, J=3.12, 1 Hz), 8.60 (brs, 1H); MS Calcd.: 154. Found 155 (M+H).

後処理

  1. waitThe solution was then brought to 65° C. for 0.5 h
  2. temperatureThe reaction mixture was then cooled
  3. customflash chromatographed with AcOEt
  4. additionProduct containing fractions
  5. concentrationwere concentrated

出典と根拠

ORDレコード
ord-09e5db3a685c45af857d343676b3d26f
出典データセット
uspto-grants-2016_09
特許番号
US09447100B2

関連ノート

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