تفاعل #3879

معادلة التفاعل

N-methylmorpholine

t-butoxycarbonylphenylalanine

N-methylmorpholine

methyl 5-aminopentanoate hydrochloride

isobutylchloroformate

→

title compound

المردود 96.2%

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

المردود 96.2%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter warming
2. 2
   أخرىat ca. -15°
3. 3
   أخرىfor about ten minutes
4. 4
   أخرىwas recooled to ca. -39°
5. 5
   أخرىSolvent and other volatiles were removed by concentration in vacuo
6. 6
   أخرىThe residue was triturated with ethyl acetate, which
7. 7
   غسيلwas then washed successively with water, 0.5M potassium bisulfate, water
8. 8
   تجفيفagain with 0.5M potassium bisulfate, and then dried over magnesium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated to a white solid
11. 11
    أخرىAfter collection
12. 12
    غسيلthe white solid was washed thoroughly with Skellysolve B

الإجراء التجريبي

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.

المصدر