Lithium Hydroxide → n-Tert-butoxycarbonyl-1-morpholin-4-yl-1-oxo-3-(phenylthio)propan-2-amine

HRID 2356056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356056
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([O:20]C)=O)[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCN=C=NCCCN(C)C>CO.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:10][S:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

9

Edukt 4

HCID 3939Lithium HydroxideHCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

Produkt 1

HCID 22730433n-Tert-butoxycarbonyl-1-morpholin-4-yl-1-oxo-3-(phenylthio)propan-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Example 175A (600 mg, 1.92 mmol) and 2M aqueous lithium hydroxide (4 mL) in methanol (10 mL) at room temperature was stirred for 5 hours and concentrated. The concentrate was treated with morpholine (263 mg, 3 mmol), EDCI (555 mg, 2.88 mmol), DMAP (20 mg) and DMF (20 mL), stilled for 16 hours, diluted with ethyl acetate (100 mL), washed sequentially with water (50 mL), and brine (20 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 367 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated
  2. washwashed sequentially with water (50 mL), and brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a475ddf1f09e46069b4b8300d83d191d
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754886B2

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