تفاعل #2015

معادلة التفاعل

BOP

D-Tryptophan allyl ester

triethylamine

N-benzyloxycarbonyl-α-methylalanine

→

desired product

المردود 84.5%

(R)-α-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester

المردود 84.5%

المذيبات

—

hexanes

ethyl acetate

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction quenched with saturated brine (5 ml)
2. 2
   أخرىThe methylene chloride layer was separated
3. 3
   تجفيفdried with magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىthe volatiles removed under reduced pressure
6. 6
   أخرىto leave a dark brown oil

الإجراء التجريبي

D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1).

المصدر