Triethylamine → tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamate

HRID 631992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631992
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:19].F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CNC>CN(C=O)C.O>[CH3:17][N:18]([CH3:19])[C:10]([C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 151085042-(((Tert-butoxy)carbonyl)amino)-2-ethylbutanoic acid

Produkt 1

HCID 86674741tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamateAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(tert-butoxycarbonylamino)-2-ethylbutanoic acid ((200 mg, 0.87 mmol), HATU (CAN 148893-10-1, 660 mg, 1.74 mmol) and triethylamine (CAN 121-44-8, 260 mg, 2.61 mmol) was added to a solution of dimethylamine hydrochloride (CAN 506-59-2, 117 mg, 1.74 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature. The mixture was added to water (20 mL) and extracted with ethyl acetate (30 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether) to give the product (120 mg, 53.7%); MS (EI): m/e=259.2 [M+H]+

Aufarbeitung

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-7b29783a6f3a4fbeb563255a8cbc8525
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

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