反応 #3879

反応方程式

N-methylmorpholine

t-butoxycarbonylphenylalanine

N-methylmorpholine

methyl 5-aminopentanoate hydrochloride

isobutylchloroformate

→

title compound

収率 96.2%

t-butoxycarbonyl-N-(5-methoxy-5-oxopentyl)-L-phenylalaninamide

収率 96.2%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度After warming
2. 2
   その他at ca. -15°
3. 3
   その他for about ten minutes
4. 4
   その他was recooled to ca. -39°
5. 5
   その他Solvent and other volatiles were removed by concentration in vacuo
6. 6
   その他The residue was triturated with ethyl acetate, which
7. 7
   洗浄was then washed successively with water, 0.5M potassium bisulfate, water
8. 8
   乾燥again with 0.5M potassium bisulfate, and then dried over magnesium sulfate
9. 9
   ろ過filtered
10. 10
    濃縮concentrated to a white solid
11. 11
    その他After collection
12. 12
    洗浄the white solid was washed thoroughly with Skellysolve B

実験手順

To a cold (ca -30° ), stirred solution of 26.5 g (0.1 mole) of t-butoxycarbonylphenylalanine (BOC-Phe) and 11.2 g (0.1 mole) of N-methylmorpholine in 150 ml of dimethylformamide (DMF) was added dropwise 13.2 ml (0.1 mole) of isobutylchloroformate. After warming and then holding the temperature at ca. -15° for about ten minutes, the solution was recooled to ca. -39°. To the cold mixture was added additional N-methylmorpholine (12.3 ml, ca. 0.11 mole), followed by 18.5 g (0.11 mole) of methyl 5-aminopentanoate hydrochloride. The mixture was allowed to warm to room temperature and to stand overnight. Solvent and other volatiles were removed by concentration in vacuo. The residue was triturated with ethyl acetate, which was then washed successively with water, 0.5M potassium bisulfate, water, and again with 0.5M potassium bisulfate, and then dried over magnesium sulfate, filtered, and concentrated to a white solid. After collection, the white solid was washed thoroughly with Skellysolve B to give 36.4 g of the title compound, m.p. 98°-100°. Recrystallization from ethyl acetate/Skellysolve B afforded analytically pure crystals.

出典