Water → HCID 86613531, Verbindung

HRID 2237732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2237732
[NH2:1][CH2:2][C@@H:3]([C@@H:5]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:13]=1)[CH:8]([CH3:10])[CH3:9])[OH:4].N1C=CC=CC=1.[C:40](OC(=O)C)(=[O:42])[CH3:41].O>ClCCl>[C:40]([NH:1][CH2:2][C@@H:3]([C@@H:5]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:13]=1)[CH:8]([CH3:10])[CH3:9])[OH:4])(=[O:42])[CH3:41]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59588942HCID 59588942, Verbindung

Produkt 1

HCID 86613531HCID 86613531, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The solution of 0.040 g of tert-butyl {1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate in 2 ml of dichloromethane is admixed successively with 0.007 ml of pyridine and 0.011 ml of acetic anhydride and stirred at room temperature over 1 hour. The reaction solution is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with 1M HCl, 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 colourless oil. Rf=0.37 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=17.25 (gradient II).

Aufarbeitung

  1. extractionextracted with tert-butyl methyl ether (2×)
  2. washThe combined organic phases are washed with 1M HCl, water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-35e5681758ff424ab140801b5676a29d
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718675B2

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