Dimethylamine → HCID 72455647, Verbindung

HRID 1504835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504835
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22]([OH:24])=O)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:27].F[P-](F)(F)(F)(F)F.CNC.C(N(CC)CC)C>CN(C=O)C.O>[C:18]([O:17][C:15]([NH:14][CH:13]([C:22]([N:26]([CH3:27])[CH3:25])=[O:24])[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:16])([CH3:19])([CH3:20])[CH3:21]

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 2755950Boc-dap(Z)-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 72455647HCID 72455647, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine (10.0 g, 30.0 mmol) in DMF (100 mL) was added HATU (14.0 g, 36.0 mmol). After 2 hours, dimethylamine (4.9 g, 60 mmol) and triethylamine (15.0 g, 149 mmol) were added. After 16 hours, the reaction mixture was diluted with water and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (acetonitrile/water gradient) to give benzyl {2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)-3-oxopropyl}carbamate. MS ESI calc'd. for C18H28N3O5 [M+H]+ 366. found 366. 1H NMR (400 MHz, CD3OD) δ 7.33-7.31 (m, 5H), 5.31-5.20 (m, 2H), 4.61-4.48 (m, 1H), 2.93 (s, 3H), 2.87 (s, 3H), 2.74-2.71 (m, 1H), 2.71-2.68 (m, 1H), 1.43 (s, 9H).

Aufarbeitung

  1. waitAfter 16 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse phase HPLC (acetonitrile/water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-a50784830ad34aef873efecd5a2436c2
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216173B2

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