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

HRID 1358209노트

반응식

HRID 1358209 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-3a4f8c9182b244efbb4d45d38e64b8df
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596711B1

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