tert-Butanol → HCID 67357680, compound

HRID 268905Notes

Reaction equation

HRID 268905 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11]C(O)=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>>[C:45]([O:49][C:26](=[O:35])[NH:23][CH2:11][CH:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([CH3:48])([CH3:47])[CH3:46]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59831915HCID 59831915, compound

Product 1

HCID 67357680HCID 67357680, compoundYield 19%

Procedure

To a solution of 3-(1H-indol-5-yl)-3-phenyl-propionic acid CCLXXIV (0.43 g, 1.6 mmol) in tert-butanol (10 mL) was added, under nitrogen atmosphere, triethylamine (0.18 g, 1.8 mmol), followed by diphenylphosphoryl azide (0.49 g, 1.8 mmol) and the resulting mixture was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and evaporated under reduced pressure to a syrup. This residue was diluted with ethyl acetate (50 mL) and washed with an aqueous solution of citric acid (5%), water, a saturated aqueous solution of sodium bicarbonate and brine (ca. 10-20 mL of each solution). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to a light brown film. This crude residue was purified by flash chromatography (hexane/EtOAc, 100/0 to 75/25) to give 0.10 g (19% yield) of [2-(1H-indol-5-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester CCLXXV as a colorless film.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. customevaporated under reduced pressure to a syrup
  4. additionThis residue was diluted with ethyl acetate (50 mL)
  5. washwashed with an aqueous solution of citric acid (5%), water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure to a light brown film
  9. customThis crude residue was purified by flash chromatography (hexane/EtOAc, 100/0 to 75/25)

Sources & evidence

ORD record
ord-c117e007b885483485e29d1fcdc310eb
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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