Triethylamine → 2-(2-(Tert-butoxycarbonylmethylamino)anilin-5-yl)benzoxazole

HRID 74273

Reaction equation

HRID 74273 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.Cl.[C:21]([O:25][C:26](=[O:29])[CH2:27][NH2:28])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C.[H][H]>C(#N)C.[C].[Pd].O>[C:21]([O:25][C:26]([CH2:27][NH:28][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[NH2:17])=[O:29])([CH3:24])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674983332-(2-(Tert-butoxycarbonylmethylamino)anilin-5-yl)benzoxazoleYield 40%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (0.77 g, 3.0 mmol) in acetonitrile (10 mL) was added glycine tert-butyl ester hydrochloride (0.60 g, 3.6 mmol) and triethylamine (0.90 g, 9.0 mmol), and this was heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (50 mL) of the residue obtained was added 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred overnight at room temperature. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (0.40 g, 40% yield) as a light orange solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (50 mL) of the residue obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-898cba68b6dd4b37bafc145cf3085679
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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