Acetic Anhydride → 5-[2-(S)-Acetylamino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20352

Reaktionsgleichung

Reaktionsgleichung von HRID 20352
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:17]([O:21][C:22]([N:24]1[C@@H:29]([C@@H:30]([OH:41])[C@@H:31]([NH2:40])[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=2)[CH2:28][O:27][C@@H:26]([O:42][CH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C@@H:25]1[CH3:48])=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(OCC)(=O)C>[C:17]([O:21][C:22]([N:24]1[CH:29]([C@@H:30]([OH:41])[C@@H:31]([NH:40][C:1](=[O:3])[CH3:2])[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=2)[CH2:28][O:27][C@@H:26]([O:42][CH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C@@H:25]1[CH3:48])=[O:23])([CH3:19])([CH3:18])[CH3:20]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 685615745-(R)-[2-(S)-Amino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl ester

Produkt 1

HCID 685636245-[2-(S)-Acetylamino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl esterAusbeute 34,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add acetic anhydride (320 μL, 3.4 mmol) and N,N-diisopropylethylamine (590 μL, 3.4 mmol) to a solution of 5-(R)-[2-(S)-amino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(R)-(2,2-dimethylpropoxy)-3-(S)-methylmorpholine-4-carboxylic acid tert-butyl ester (770 mg, 1.70 mmol). Stir for 2.5 hours. Dilute with ethyl acetate, wash with 1 N hydrochloric acid (twice), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 20:80 to 25:75 ethyl acetate:hexanes) to give the desired compound (292 mg).

Aufarbeitung

  1. washwash with 1 N hydrochloric acid (twice), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 20:80 to 25:75 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fbe26c185e70421fb7475c93b15b63c2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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