Diisopropylethylamine → tert-butyl N-[N-[(2S)-2-(2,4,6-trimethylphenoxy)propanoyl]carbamimidoyl]carbamate

HRID 873777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873777
[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][C@@H:10]([CH3:14])[C:11]([OH:13])=O.C([N:19](C(C)C)CC)(C)C.N[N:26]([CH:34]=[NH:35])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[NH:19]=[C:34]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[NH:35][C:11](=[O:13])[C@@H:10]([O:9][C:2]1[C:1]([CH3:15])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8])[CH3:14]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 36689000(2S)-2-(Mesityloxy)propionic acidHCID 86691067Tert-butyl amino(imino)methylcarbamate

Produkt 1

HCID 149434102tert-butyl N-[N-[(2S)-2-(2,4,6-trimethylphenoxy)propanoyl]carbamimidoyl]carbamateAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(2S)-2-(Mesityloxy)propionic acid (5.6 g; 27 mmol), diisopropylethylamine (17.3 g; 133 mmol), tert-butyl amino(imino)methylcarbamate (4.3 g; 27 mmol), and 1-hydroxybenzotriazole monohydrate (4.1 g; 27 mmol) were dissolved in N,N-dimethylformamide (80 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (10.2 g; 27 mmol) was added, and the mixture was stirred for 137 hours at room temperature. To the reaction solution, ethyl acetate (400 mL) was added, and the mixture was washed sequentially with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure, to give 8.6 g of the title compound (yield 91%) as an oil.

Aufarbeitung

  1. washthe mixture was washed sequentially with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8d5de1ba8b2649ecb50f328f2e9ff9f3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975411B2

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