تفاعل #3023

معادلة التفاعل

methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(benzyloxycarbonylamino)pentyl}carbamoyl]indol-1-yl}acetate

→

methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate

المردود 85.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe reaction mixture is left at 30° C.
2. 2
   درجة الحرارةwhile maintaining this pressure
3. 3
   درجة الحرارةAfter cooling
4. 4
   ترشيحthe catalyst is filtered over a bed of celite and evaporation
5. 5
   أخرىThe residual oil is purified by flash chromatography on silica gel, eluent

الإجراء التجريبي

5.6 g of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(benzyloxycarbonylamino)pentyl}carbamoyl]indol-1-yl}acetate (EXAMPLE 66) are dissolved in 170 ml of methanol and 0.56 g of 10% Pd/C is added thereto. Hydrogenation is carried out under a pressure of 3 bar and the reaction mixture is left at 30° C., while maintaining this pressure, for 18 hours. After cooling, the catalyst is filtered over a bed of celite and evaporation is carried out to dryness. The residual oil is purified by flash chromatography on silica gel, eluent: CH2Cl2 /CH3 OH/AcOH 90/10/0.5 (v/v/v) in order to obtain white crystals of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate, M.p.=78° C., [α]D20 =-47.6° (c=1, CH3OH), Yield: 85%.

المصدر