Dimethylformamide → HCID 68749501, Verbindung

HRID 333351

Reaktionsgleichung

Reaktionsgleichung von HRID 333351
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH3:8].[C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17](O)=[O:18])=[CH:11][CH:10]=1.CN(C=O)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:9]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C:17]([N:7]([CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH3:8])=[O:18])=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 78492N-MethylfurfurylamineHCID 2761796N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 68749501HCID 68749501, VerbindungAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(furan-2-yl)-N-methylmethanamine (195 mg, 1.76 mmol), (S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid (500 mg, 1.45 mmol), in CH2Cl2 (3 mL) and DMF (3 mL) was added TEA (0.61 mL, 4.39 mmol) and HATU (724 mg, 1.90 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was quenched with aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with aq. NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography using 30%-EtOAc/heptane to 90% EtOAc/heptane to give (S)-tert-butyl 3-(biphenyl-4-yl)-1-((furan-2-ylmethyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (614 mg). HPLC retention time=1.80 minutes (condition B); MS (m+1)=435.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.31 (s, 9H, minor rotamer), 1.34 (s, 9H, major rotamer), 2.61 (s, 3H, major rotamer), 2.83 (s, 3H, minor rotamer), 2.87-2.98 (m, 4H), 4.15-4.32 (m, 2H, minor isomer), 4.20 (d, J=15.1 Hz, 1H, major rotamer), 4.62 (d, J=15.1 Hz, 1H, major rotamer), 4.77 (q, J=7.3 Hz, 1H, major rotamer), 4.95 (q, J=7.3 Hz, 1H, minor rotamer), 5.30 (d, J=8.6 Hz, 1H, minor rotamer), 5.39 (d, J=8.6 Hz, 1H, major rotamer), 6.05 (d, J=2.8 Hz, 1H, minor rotamer), 6.10 (d, J=2.8 Hz, 1H, major rotamer), 6.18 (br. s., 1H, minor rotamer), 6.23 (dd, J=3.2, 1.9 Hz, 1H, major rotamer), 7.10-7.50 (m, 18H).

Aufarbeitung

  1. customThe mixture was quenched with aq. NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with aq. NaHCO3, water, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3deee59742614319871bcc04a74b46a9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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