Ammonium Hydroxide → Ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinate

HRID 1358209ノート

反応式

HRID 1358209 の反応式
[CH2:1]([O:3][P:4]([CH2:7][CH:8]([F:14])[C:9](OCC)=[O:10])([CH3:6])=[O:5])[CH3:2].[OH-].[NH4+:16]>C(O)C>[NH2:16][C:9](=[O:10])[CH:8]([F:14])[CH2:7][P:4]([CH3:6])(=[O:5])[O:3][CH2:1][CH3:2]

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 18184129Ethyl 3-[ethoxy(methyl)phosphoryl]-2-fluoropropanoate

生成物 1

HCID 86759072Ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinate収率 86.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl 3-[ethoxy(methyl)phosphoryl]-2-fluoropropanoate (12.6 g, 55.6 mmol), ethanol (15 mL), and concentrated ammonium hydroxide (14.8 N, 5.6 mL, 83 mmol) were stirred at room temperature for 16 h. The solvent was evaporated and the residue chromatographed on a wet-packed silica gel column (5.5×31 cm) eluting with 90:10 methylene chloride/methanol. The appropriate fractions were combined and evaporated to give 9.5 g (86%) of ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinate as a clear oil. Data: 1H NMR (300 MHz, CDCl3) δ6.62 (s, 1H), 6.33 (s, 1H), 5.10-5.42 (m, 1H), 4.02-4.18 (m, 2H), 2.19-2.70 (m, 2H), 1.60 (d, J=14 Hz, 3H), 1.34 (m, 3H)

後処理

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on a wet-packed silica gel column (5.5×31 cm)
  3. washeluting with 90:10 methylene chloride/methanol
  4. customevaporated

出典と根拠

ORDレコード
ord-3a4f8c9182b244efbb4d45d38e64b8df
出典データセット
uspto-grants-2003_07
特許番号
US06596711B1

反応ノート

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