Water → tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate

HRID 23214ノート

反応式

HRID 23214 の反応式
Cl[CH2:2][C@@H:3]([OH:22])[C@@H:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([F:13])[CH:7]=1.[OH-].[K+].O>C(O)C>[F:13][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:3]2[CH2:2][O:22]2)[CH:11]=[C:10]([F:12])[CH:9]=1

参加物

5

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11473133(1S,2S)-[3-Chloro-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

生成物 1

HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a 250 mL 3-neck round bottom flask equipped with magnetic stir bar, nitrogen inlet and thermocouple, is added tert-butyl (1S,2S)-3-chloro-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate IV, EXAMPLE 3, 3.5 g, 0.010 moles, 1 equivalent) followed by absolute ethanol (60 mL) and cooled to 0°. To this mixture is added potassium hydroxide (0.73 g, 0.013 moles, 1.25 equivalents) dissolved in absolute ethanol (10 mL) over 1 hr and the resulting suspension is warmed to 15-20° and stirred for 1 hr. At this time, water (100 mL) is added and the reaction contents are cooled to −5° and stirred for 30 min. The solids are collected by filtration and washed with cold water (2×25 mL) then dried under reduced pressure at 450 to give the title compound, mp=133°; NMR (DMSO-d6) δ 7.03, 3.61, 2.68-2.98 and 1.33; CMR (DMSO-d6) δ 163.72, 161.29, 155.55, 143.35, 112.65, 101.80, 78.17, 53.42, 52.71, 44.90, 36.98 and 28.36.

後処理

  1. customTo a 250 mL 3-neck round bottom flask equipped with magnetic stir bar, nitrogen inlet
  2. temperaturecooled to 0°
  3. temperaturethe resulting suspension is warmed to 15-20°
  4. customthe reaction contents
  5. temperatureare cooled to −5°
  6. stirringstirred for 30 min
  7. filtrationThe solids are collected by filtration
  8. washwashed with cold water (2×25 mL)
  9. customthen dried under reduced pressure at 450

出典と根拠

ORDレコード
ord-f2a7a6812f994def84962ac1f4477fb9
出典データセット
uspto-grants-2005_02
特許番号
US06849750B2

反応ノート

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