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Water → Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate

HRID 1527131
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1527131
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([C:20]([O:24][N:25]1N=NC2C=CC=N[C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O>C(Cl)Cl>[CH3:20][O:24][N:25]([CH3:26])[C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 57449675Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate
Ausbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (10 g, 43 mmol) in DCM (60 mL) was added HATU (19 g, 50 mmol) in portions, The mixture was stirred at room temperature for 0.5 h. Then DIPEA (12.9 g, 100 mmol) and N, O-dimethylhydroxylamine hydrochloride (5.0 g, 51.5 mmol) were added in the mixture. The mixture was stirred at room temperature overnight. Water (40 mL) was added and the mixture was extracted by DCM (100 mL*3). The organic layer was washed with brine (5 mL) and dried over sodium sulfate. Concentration and purification by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=20/1-10/1) to give tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (10 g, 84%).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted by DCM (100 mL*3)
  3. washThe organic layer was washed with brine (5 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=20/1-10/1)

Quellen und Nachweise

ORD-Eintrag
ord-1b348b3be3b3466e8233d08c6a6cd06c
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09085583B2

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