Pyridine → (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-nitrobenzylsulphonyl)valerohydrazide

HRID 1386560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386560
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].[N+:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][S:44](Cl)(=[O:46])=[O:45])([O-:36])=[O:35].N1C=CC=CC=1>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[S:44]([CH2:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[N+:34]([O-:36])=[O:35])(=[O:45])=[O:46])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 4305447(2-nitrophenyl)methanesulfonyl ChlorideHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Produkt 1

HCID 86757177(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-nitrobenzylsulphonyl)valerohydrazideAusbeute 109,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 0.689 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS) -pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 8 ml of dichloromethane was treated with 0.236 g of 2-nitro-α-toluenesulphonyl chloride and 0.152 ml of pyridine at room temperature and under a nitrogen atmosphere. The mixture was stirred for 2 hours and evaporated. The residue was dissolved in ethyl acetate and washed in sequence with water, 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulphate. Evaporation and trituration of the residue with diethyl ether gave 0.72 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(2-nitrobenzylsulphonyl)valerohydrazide in the form of a white solid.

Aufarbeitung

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed in sequence with water, 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customEvaporation and trituration of the residue with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-706e871b77c940c7ba4266c8f3ea18b7
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265446B1

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