Triethylamine → N-[(9H-Xanthen-9-yl)methyl]-N'-{2-t-butyl-5-[4-cyclohexyl-3-(t-butyldimethylsilyloxy)butyl]phenyl}urea

HRID 1734900노트

반응식

HRID 1734900 반응식
[CH:1]1[C:14]2[CH:13]([CH2:15]C(O)=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[C:43]([C:47]1[CH:53]=[CH:52][C:51]([CH2:54][CH2:55][CH:56]([O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:67])[CH3:66])[CH2:57][CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]2)=[CH:50][C:48]=1[NH2:49])([CH3:46])([CH3:45])[CH3:44]>C1C=CC=CC=1.C(OCC)(=O)C>[CH:11]1[C:12]2[CH:13]([CH2:15][NH:38][C:41]([NH:49][C:48]3[CH:50]=[C:51]([CH2:54][CH2:55][CH:56]([O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:66])[CH3:67])[CH2:57][CH:58]4[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]4)[CH:52]=[CH:53][C:47]=3[C:43]([CH3:46])([CH3:44])[CH3:45])=[O:26])[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[O:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 8346622-(9H-xanthen-9-yl)acetic acidHCID 199662172-t-Butyl-5-[4-cyclohexyl-3-(t-butyldimethylsilyloxy)butyl]aniline

생성물 1

HCID 19966060N-[(9H-Xanthen-9-yl)methyl]-N'-{2-t-butyl-5-[4-cyclohexyl-3-(t-butyldimethylsilyloxy)butyl]phenyl}urea수율 65%

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 240 mg (1.00 mmol) of 2-(9H-xanthen-9-yl)acetic acid, 275 mg (1.00 mmol) of diphenylphosphoryl azide and 139 μl (1.00 mmol) of triethylamine in 3 ml of benzene was heated under reflux, with stirring, for 2.5 hours, after which a solution of 459 mg (1.10 mmol) of 2-t-butyl-5-[4-cyclohexyl-3-(t-butyldimethylsilyl-oxy)butyl]aniline in 0.5 ml of benzene was added. The resulting mixture was heated under reflux for 3 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate, and the diluted mixture was washed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 25 g of silica gel, using a 95:5 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 414 mg (yield 65%) of the title compound as a foam-like material.

후처리

  1. temperatureunder reflux
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 3 hours
  4. washthe diluted mixture was washed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 25 g of silica gel
  8. additionby volume mixture of methylene chloride and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-7dc96d4498184b73aa53071c9b8dda77
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534529

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