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

HRID 977861Notes

Reaction equation

HRID 977861 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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-butyldimethylsilyloxy)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.

Workup

  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

Sources & evidence

ORD record
ord-ea2d9747b10a4588992b0769c43859b4
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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