Sodium hydride → N-{2-t-Butyl-5-[2-(oxiran-2-yl)ethyl]phenyl}-2-(9H-xanthen-9-yl)acetamide

HRID 977883노트

반응식

HRID 977883 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]=[O:22])=[CH:15][C:14]=1[NH:23][C:24](=[O:40])[CH2:25][CH:26]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:33][C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)([CH3:12])([CH3:11])[CH3:10]>O1CCCC1.C(OCC)(=O)C>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]2[CH2:4][O:22]2)=[CH:15][C:14]=1[NH:23][C:24](=[O:40])[CH2:25][CH:26]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:33][C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)([CH3:12])([CH3:10])[CH3:11]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 19966225HCID 19966225, 화합물

생성물 1

HCID 19966191N-{2-t-Butyl-5-[2-(oxiran-2-yl)ethyl]phenyl}-2-(9H-xanthen-9-yl)acetamide수율 65%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 690 mg (15.8 mmol) of sodium hydride (as a 55% w/w dispersion in mineral oil, which had previously been washed with hexane) in 10 ml of dimethyl sulfoxide was stirred for 30 minutes, after which 2.66 g (12.1 mmol) of trimethylsulfoxonium iodide were added. The resulting mixture was stirred for 1 hour at 40° C., and then a solution of 4.50 g (10.5 mmol) of N-[2-t-butyl-5-(3-oxopropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 19) in 25 ml of tetrahydrofuran was added dropwise over a period of 5 minutes. The reaction mixture was then stirred for 1 hour, after which the reaction mixture was cooled to room temperature and then diluted with ethyl acetate. The diluted mixture was washed several times with water and once with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 250 g of silica gel, using a 9:1 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 3.00 g (yield 65%) of the title compound as crystals, melting at 156°-157° C. (after recrystallization from a mixture of ethyl acetate and hexane).

후처리

  1. washhad previously been washed with hexane) in 10 ml of dimethyl sulfoxide
  2. stirringThe resulting mixture was stirred for 1 hour at 40° C.
  3. stirringThe reaction mixture was then stirred for 1 hour
  4. washThe diluted mixture was washed several times with water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 250 g of silica gel
  8. additionby volume mixture of methylene chloride and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-3aec9a9e3eab451bb4c767de5c8c3a77
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614550

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