Potassium Carbonate → (S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

HRID 25237

반응식

HRID 25237 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[N+](C1C=C(S(O[CH2:25][C@H:26]2[O:28][CH2:27]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:25][C@H:26]1[O:28][CH2:27]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 41154952-Amino-3-Nitrophenol

생성물 1

HCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane수율 84.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

5 g (0.032 mol) of 2-amino-3-nitrophenol, 8 g (0.032 mol) of (S)-(+)-glycidyl 3-nitrobenzenesulfonate and 8.9 g of K2CO3 are mixed in 80 ml of acetone and the mixture is refluxed for 18 hours. Filtration is carried out, the solvent is evaporated under reduced pressure and the crude product is purified by flash chromatography, elution being carried out with a 7/3 cyclohexane/ethyl acetate mixture. The solid product obtained is triturated in ethyl ether and 5.67 g of the title product are obtained. M.p.: 107-109°. αD+28.1 (c=0.5%, MeOH).

후처리

  1. temperaturethe mixture is refluxed for 18 hours
  2. filtrationFiltration
  3. customthe solvent is evaporated under reduced pressure
  4. customthe crude product is purified by flash chromatography, elution
  5. customThe solid product obtained
  6. customis triturated in ethyl ether

출처 및 근거

ORD 기록
ord-f4b14f780c4148528ec5549cc4115d8e
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858629B1

연결된 노트

불러오는 중…