Ethyl Acetate → HCID 12016496、化合物

HRID 1264616ノート

反応式

HRID 1264616 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:28]([O-])=O)=[C:6]([CH:27]=1)[CH2:7][N:8]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11].O.O.[Sn](Cl)(Cl)(Cl)Cl.[C:38]([O-])(O)=O.[Na+].C(O[CH2:47][CH3:48])(=O)C>C(O)C>[NH2:28][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:27][C:6]=1[CH2:7][N:8]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:38]#[C:47][CH3:48])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18612902HCID 18612902、化合物HCID 85782573Tin tetrachloride dihydrate

生成物 1

HCID 12016496HCID 12016496、化合物収率 58%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Methyl 2-{(5-fluoro-2-nitrobenzyl)[(4-methoxyphenyl)sulfonyl]amino}-3-hydroxypropanoate (1.0 g, 2.08 mmol) was dissolved in ethanol (18 mL). To this was added tin chloride dihydrate (2.35 g, 10.4 mmol) and the reaction was heated to 70° C. for 2 hours. The reaction was then cooled to room temperature and ice water followed by NaHCO3 was added to bring the solution to pH 8. Ethyl acetate was added and the suspension was filtered through celite. The organic layer was separated and washed with brine, dried over Na2SO4 concentrated in vacuo and chromatographed using 1:1 hexane:ethyl acetate as eluant to provide 0.55 g (58%) of the desired product as a yellow oil.

後処理

  1. temperatureThe reaction was then cooled to room temperature
  2. additionwas added
  3. filtrationthe suspension was filtered through celite
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customchromatographed

出典と根拠

ORDレコード
ord-c775419fbf1d4407a48e9b8f18c7a213
出典データセット
uspto-grants-2003_04
特許番号
US06544984B1

反応ノート

読み込み中…