Dichloromethane → 5(S)-Amino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid (N-(1-carbamoyl-1-methyl-ethyl)]-amide hydrochloride

HRID 2256755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256755
FC(F)(F)C(O)=O.[C:8]([C:11]([NH:14][C:15](=[O:52])[C@H:16]([CH:49]([CH3:51])[CH3:50])[CH2:17][C@H:18]([OH:48])[C@@H:19]([NH:40]C(OC(C)(C)C)=O)[CH2:20][C@@H:21]([CH:37]([CH3:39])[CH3:38])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:24]=1)([CH3:13])[CH3:12])(=[O:10])[NH2:9].[OH-].[Na+].[Cl:55]CCl>>[ClH:55].[C:8]([C:11]([NH:14][C:15](=[O:52])[C@H:16]([CH:49]([CH3:51])[CH3:50])[CH2:17][C@H:18]([OH:48])[C@@H:19]([NH2:40])[CH2:20][C@@H:21]([CH:37]([CH3:39])[CH3:38])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:24]=1)([CH3:13])[CH3:12])(=[O:10])[NH2:9]

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 236270705(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(1-carbamoyl-1-methyl-ethyl)]-amide

Produkt 1

HCID 236264245(S)-Amino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid (N-(1-carbamoyl-1-methyl-ethyl)]-amide hydrochloride

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.5 ml of trifluoroacetic acid are added to 56 mg of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(1-carbamoyl-1-methyl-ethyl)]-amide in 1.5 ml of dichloromethane at 0° C. The mixture is stirred for a further 30 minutes at 0° C. The reaction mixture is poured onto cooled 1N sodium hydroxide and the product is extracted repeatedly with dichloromethane. The organic phases are dried, and ethereal hydrochloric acid is added. Concentration by evaporation yields the title compound: Rf (dichloromethane/methanol=8:2)=0.30; HPLC Rt =11.25; FAB-MS (M+H)+ =538.

Aufarbeitung

  1. additionThe reaction mixture is poured
  2. extractionthe product is extracted repeatedly with dichloromethane
  3. customThe organic phases are dried
  4. additionethereal hydrochloric acid is added
  5. concentrationConcentration
  6. customby evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0ecbca7153014e85bc777535fddbff22
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05654445

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