Dimethylformamide → HCID 86671822, Verbindung

HRID 2038796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038796
C(C1CCC1(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.CN([C:19]([O:23][N:24]1N=NC2C=CC=N[C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN[O:43][CH3:44].[CH:45](N(C(C)C)CC)([CH3:47])[CH3:46].C[N:55]([CH:57]=[O:58])[CH3:56]>CCOC(C)=O.O>[C:4]([O:3][C:57](=[O:58])[NH:55][C:56]1([C:44](=[O:43])[N:24]([O:23][CH3:19])[CH3:25])[CH2:47][CH2:45][CH2:46]1)([CH3:5])([CH3:6])[CH3:7]

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67516526HCID 67516526, Verbindung

Produkt 1

HCID 86671822HCID 86671822, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Boc-1-aminocyclobutane-1-carboxylic acid (10.0 g, 45.1 mmol), HATU (20.5 g, 54.1 mmol) and N,O-dimethylhydroxylamine hydrochloride (4.93 g, 49.6 mmol) were combined in DMF (100 mL). To this solution was added diisopropylethylamine (31.4 mL, 180.3 mmol). The reaction was stirred for 2 h, diluted with EtOAc and poured into H2O. The aqueous phase was separated and extracted two more times with EtOAc. The organic layers were combined and washed with brine, dried (Na2SO4), decanted and concentrated in vacuo. The resultant solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane) to afford [1-(methoxy-methyl-carbamoyl)-cyclobutyl]-carbamic acid tert-butyl ester as a white solid (11.5 g, 99%).

Aufarbeitung

  1. customThe aqueous phase was separated
  2. extractionextracted two more times with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe resultant solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-4fb7dd28c12f48f2871c4ddbd9efd407
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575360B2

Notizen zur Reaktion

Wird geladen…