Dithiaoctanediol → Z-(S)-[1-(2-{4-[3-(4-Chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid-tert.-butyl ester

HRID 1862495

Reaktionsgleichung

Reaktionsgleichung von HRID 1862495
[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([C:12](=[O:35])[NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:18]([O:33][CH3:34])[CH:17]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(O)CSCCSCCO>O1CCCC1.[Pd]>[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([C:12](=[O:35])[NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23]/[CH:24]=[CH:25]\[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:18]([O:33][CH3:34])[CH:17]=1)[CH:9]([CH3:10])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 2

HCID 78904Dithiaoctanediol2×HCID 22982866(S)-[1-(2-{4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-3-methoxy-phenyl}ethylcarbamoyl)-2-methyl-propyl]-carbamic acid-tert.-butyl ester

Produkt 1

HCID 69822741Z-(S)-[1-(2-{4-[3-(4-Chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid-tert.-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To (S)-[1-(2-{4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-3-methoxy-phenyl}ethylcarbamoyl)-2-methyl-propyl]-carbamic acid-tert.-butyl ester (18 g) in tetrahyrofuran (180 ml), Lindlar-catalyst (5%-Pd on CaSO4; 7.2 g), 3,6-dithia-1,8-octandiol (45 mg) and 2,2′-(ethylenedithio)-diethanol (45 mg) are added. The resulting mixture is shaken under a hydrogen atmosphere at room temperature and at normal pressure for 5 hours. It is then filtered and evaporated. The residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:2) and recrystallised (ethyl acetate/hexane). Z-(S)-[1-(2-{4-[3-(4-Chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid-tert.-butyl ester is obtained, m.p. 82-84° C.

Aufarbeitung

  1. filtrationIt is then filtered
  2. customevaporated
  3. customThe residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:2)
  4. customrecrystallised (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2583a6e03fc3407cadc8fc825412acc5
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06538016B2

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