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Methylamine → (S)-tert-butyl 3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamate

HRID 333348
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333348
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:9](O)=[O:10])=[CH:3][CH:2]=1.[CH3:26][N:27](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.CN>CN(C=O)C.C(Cl)Cl>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9]([NH:27][CH3:26])=[O:10])=[CH:3][CH:2]=1
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Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 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 10498346(S)-tert-butyl 3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamate
Ausbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid (300 mg, 0.88 mmol) in DMF (1.5 mL) and DCM (1.5 mL) was added HATU (401 mg, 1.05 mmol) and triethylamine (0.37 mL, 2.64 mmol) followed by methylamine (0.46 mL, 0.91 mmol). The mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with sat NaHCO3 and extracted with EtOAc. The organic layer was washed with water (8 times), brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by TLC preparation plates using 3% 2N Ammonia in MeOH in DCM to give (S)-tert-butyl 3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamate (111 mg). HPLC retention time=1.66 minutes (condition B); MS (m+1)=355.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (s, 9H) 2.66 (d, J=4.8 Hz, 3H) 3.01 (d, J=6.3 Hz, 2H) 4.18-4.41 (m, 1H) 5.08 (br. s., 1H) 5.93 (d, J=4.3 Hz, 1H) 7.19 (d, J=8.1 Hz, 2H) 7.22-7.29 (m, 1H) 7.35 (t, J=7.6 Hz, 2H) 7.44 (d, J=8.1 Hz, 2H) 7.48 (d, J=7.3 Hz, 2H).

Aufarbeitung

  1. customThe reaction mixture was quenched with sat NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water (8 times), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by TLC preparation plates

Quellen und Nachweise

ORD-Eintrag
ord-58b369490b1b40958d8601c80a35f481
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877815B2

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