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

HRID 1480093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480093
[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=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CN>CN(C=O)C.O>[CH3:17][NH:18][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 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6364545Methylamine hydrochlorideHCID 151085042-[(tert-Butoxycarbonyl)amino]-2-ethylbutanoic acid

Produkt 1

HCID 86674754tert-Butyl 3-(methylcarbamoyl)pentan-3-ylcarbamateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(tert-butoxycarbonylamino)-2-ethylbutanoic acid (Example 45a, 400 mg, 2 mmol), HBTU (CAN 94790-37-1, 1.3 g, 3 mmol), triethylamine (0.7 g, 7 mmol) in DMF (10 mL) was stirred for 30 min, then methanamine hydrochloride (CAN 593-51-1, 260 mg, 6 mmol) was added into the mixture and the solution was stirred overnight. After that, the solution was diluted with water (20 mL) and extracted with ethyl acetate (3×30 mL), the combined organic layer was washed with water (3×50 mL) and brine (60 mL), then evaporated to dryness. The crude product (0.18 g, 45%) obtained as a light yellow solid was used for the next step directly without any purification.

Aufarbeitung

  1. stirringthe solution was stirred overnight
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washthe combined organic layer was washed with water (3×50 mL) and brine (60 mL)
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4ffd4c8182ae417b8d8a6f90b2f4a063
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409866B2

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