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

HRID 1734900ノート

反応式

HRID 1734900 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7dc96d4498184b73aa53071c9b8dda77
出典データセット
uspto-grants-1996_07
特許番号
US05534529

反応ノート

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