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Piperidine → tert-Butyl (1(S)-(1(S)-hydroxy-2-piperidin-1-ylethyl)-3(S)-{[2-(3-methoxypropoxy)-benzoylamino]methyl}-4-methylpentyl)carbamate

HRID 507826
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 507826
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:33]=[CH:32][CH:31]=[CH:30][C:8]=1[C:9]([NH:11][CH2:12][C@H:13]([CH:27]([CH3:29])[CH3:28])[CH2:14][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:16]1[CH2:18][O:17]1)=[O:10].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(O)(C)C>[OH:17][C@H:16]([C@@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14][C@H:13]([CH2:12][NH:11][C:9](=[O:10])[C:8]1[CH:30]=[CH:31][CH:32]=[CH:33][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:27]([CH3:29])[CH3:28])[CH2:18][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1
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Komponenten

4

Edukt 2

HCID 8082PiperidineHCID 86613450tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-(R)-oxiranylpentyl)-carbamate

Produkt 1

HCID 86613449tert-Butyl (1(S)-(1(S)-hydroxy-2-piperidin-1-ylethyl)-3(S)-{[2-(3-methoxypropoxy)-benzoylamino]methyl}-4-methylpentyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 0.030 g of tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)—(R)-oxiranylpentyl)carbamate in 0.60 ml of isopropanol and 0.050 ml of piperidine is stirred at 70° C. over 1 hour. The reaction mixture is concentrated by evaporation, and the residue is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.34 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.08 (gradient I).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-f27308b84bbd41b7af5af54990527682
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07786307B2

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