Hydrochloric Acid → tert-Butyl (2-carbamoylfuran-3-yl)carbamate

HRID 32595

Reaktionsgleichung

Reaktionsgleichung von HRID 32595
C([N:4](C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].[C:45]([O:49][C:50]([NH:52][C:53]1[CH:57]=[CH:56][O:55][C:54]=1[C:58]([OH:60])=O)=[O:51])([CH3:48])([CH3:47])[CH3:46].Cl>CN(C=O)C>[NH2:4][C:58]([C:54]1[O:55][CH:56]=[CH:57][C:53]=1[NH:52][C:50](=[O:51])[O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:60]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 468356103-((tert-Butoxycarbonyl)amino)furan-2-carboxylic acid2×

Produkt 1

HCID 53439236tert-Butyl (2-carbamoylfuran-3-yl)carbamateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Diisopropylethylamine (14.75 mL) was added to a suspension of PyBOP (10.4 g), ammonium chloride (1.81 g) and 3-[(tert-butoxycarbonyl)amino]-2-furoic acid (Intermediate 81) (3.83 g) in DMF (50 mL). The resulting mixture was stirred at ambient temperature for 90 minutes, poured into 0.4 M HCl (250 mL) and extracted into DCM (3×100 mL). The combined organics were washed with water (80 mL) and brine (80 mL), dried (MgSO4), and evaporated The product was purified by flash chromatography on silica, eluting with 20-70% EtOAc in isohexane to afford the title compound as a white solid (3.38 g, 89%);

Aufarbeitung

  1. extractionextracted into DCM (3×100 mL)
  2. washThe combined organics were washed with water (80 mL) and brine (80 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated The product
  5. customwas purified by flash chromatography on silica
  6. washeluting with 20-70% EtOAc in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-fc69a7ca2cf04a67bc09dcf34db3ae30
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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