Succinic anhydride → 3-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acid

HRID 1397110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397110
[C:1]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:2][NH:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl.ClCCl>[C:14]([O:13][C:1]([CH2:2][N:3]([CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])[C:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:24])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

6

Edukt 3

HCID 7922Succinic anhydrideHCID 81531DiisopropylethylamineHCID 4393691DI-T-Butyl iminodiacetate

Produkt 1

HCID 866665243-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acidAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 14 (0.88 g, 3.59 mmol), succinic anhydride (0.377 g, 3.77 mmol), ethyldiisopropylamine (625 μL, 3.59 mmol) and 4-di(methylamino)pyridine (44 mg, 0.359 mmol) were dissolved in CHCl3 (15 mL) and stirred for 48 h. The mixture was diluted with dichloromethane (140 mL) and the organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (80% EtOAc in hexanes) to give the compound 15 (0.9 g, 72.6%). 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 1.47 (s, 9H), 2.62 (t, J=5.8, 2H), 2.69 (t, J=5.8, 2H), 4.02 (s, 2H), 4.06 (s, 2H). ESI-MS calculated for C16H27NO7, 345.59 found 368.1 (M+Na).

Aufarbeitung

  1. washthe organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by silica gel chromatography (80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1418035c9c3440b891b7576b7d241d9d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901072B2

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