반응 #6479

반응 방정식

lithium hydroxide monohydrate

water

N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(5-acetoxy-pent-1-yn-1-yl)-benzenesulfonamide

→

title compound

수율 97.7%

N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(5-hydroxy-pent-1-yn-1-yl)-benzenesulfonamide

수율 97.7%

용매

methanol tetrahydrofuran

반응 조건

후처리

1. 1
   기타the solvents are evaporated off at 15 torr and 40° and 50 ml of methylene chloride
2. 2
   workup.ADDITIONare added to the residue
3. 3
   workup.ADDITIONby adding 50 ml of 1N hydrochloric acid
4. 4
   기타The organic phase is separated off in a separating funnel
5. 5
   추출The aqueous phase is extracted twice with 20 ml of methylene chloride each time
6. 6
   세척The combined organic phases are washed with semi-saturated sodium chloride solution
7. 7
   건조dried over magnesium sulfate
8. 8
   농축concentrated by evaporation at 15 torr and 40°
9. 9
   기타The residue is chromatographed on 45 g of silica gel (Merck, ST 60, 4-63 μm) with 20% hexane in ethyl acetate

실험 절차

0.37 g of lithium hydroxide monohydrate and 10 ml of water are added to a solution of 1.2 g of N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(5-acetoxy-pent-1-yn-1-yl)-benzenesulfonamide in 40 ml of methanol/tetrahydrofuran=1/1. The mixture is stirred for 16 hours at room temperature, then the solvents are evaporated off at 15 torr and 40° and 50 ml of methylene chloride are added to the residue. Acidification is effected by adding 50 ml of 1N hydrochloric acid. The organic phase is separated off in a separating funnel. The aqueous phase is extracted twice with 20 ml of methylene chloride each time. The combined organic phases are washed with semi-saturated sodium chloride solution, dried over magnesium sulfate and concentrated by evaporation at 15 torr and 40°. The residue is chromatographed on 45 g of silica gel (Merck, ST 60, 4-63 μm) with 20% hexane in ethyl acetate to yield 1.1 g of the title compound in the form of a white amorphous solid. 1H-NMR (400 MHz, DMSO-d6): 8.90 (s, b, 1H); 8.05 (m, 1H); 7.56 (m, 5H); 7.43 (d, d, 1H); 7.24 (d, 1H); 7.17 (d, d, 1H); 7.15 (d, 1H); 6.96 (s, 1H); 5.08 (m, 1H); 3.97 (s, 2H); 3.92 (s, 3H); 3.68 (s, 3H); 3.47 (t, 2H); 2.47 (t, 2H); 1.92-1.55 (m, 8H); 1.64 (m, 2H).

출처