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

HRID 6383

Reaktionsgleichung

Reaktionsgleichung von HRID 6383
O.[OH-].[Li+].O.[CH:5]1([O:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH3:23])[CH:18]=[C:17]3[CH2:24][C:25]2[CH:51]=[CH:50][C:28]([C:29]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]#[C:42][CH2:43][CH2:44][CH2:45][O:46]C(=O)C)(=[O:34])=[O:33])=[O:30])=[CH:27][C:26]=2[O:52][CH3:53])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1>CO.O1CCCC1>[CH:5]1([O:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH3:23])[CH:18]=[C:17]3[CH2:24][C:25]2[CH:51]=[CH:50][C:28]([C:29]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]#[C:42][CH2:43][CH2:44][CH2:45][OH:46])(=[O:33])=[O:34])=[O:30])=[CH:27][C:26]=2[O:52][CH3:53])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 19793624N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(5-acetoxy-pent-1-yn-1-yl)-benzenesulfonamide

Produkt 1

HCID 19793592N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(5-hydroxy-pent-1-yn-1-yl)-benzenesulfonamideAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a86cb8e6d2cf4b918a68d5f5c49a6347
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248693

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