Diisopropylethylamine → Tert-butyl({[mesityl(methyl)amino]acetyl}amino)(imino)methylcarbamate

HRID 873780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873780
[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9]([CH2:11][C:12]([OH:14])=O)[CH3:10].C(N(C(C)C)CC)(C)C.[NH2:25][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>[C:29]([O:28][C:27](=[O:33])[N:26]([NH:25][C:12](=[O:14])[CH2:11][N:9]([C:2]1[C:1]([CH3:15])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8])[CH3:10])[CH:34]=[NH:35])([CH3:32])([CH3:30])[CH3:31]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 82113003[Mesityl(methyl)amino]acetic acidHCID 86691067Tert-butyl amino(imino)methylcarbamate

Produkt 1

HCID 86691074Tert-butyl({[mesityl(methyl)amino]acetyl}amino)(imino)methylcarbamateAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

[Mesityl(methyl)amino]acetic acid (6.67 g; 32 mmol), diisopropylethylamine (20.68 g; 160 mmol), tert-butyl amino(imino)methylcarbamate (6.11 g; 38 mmol), and 1-hydroxybenzotriazole monohydrate (5.88 g; 38 mmol) were dissolved in N,N-dimethylformamide (150 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (14.56 g; 38 mmol) was added thereto, and the mixture was stirred for 65 hours at room temperature. To the reaction solution, ethyl acetate (400 mL) was added, and the mixture was washed 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. The resulting crystals were dispersed in diethyl ether, collected by filtration and dried to give 5.82 g of the title compound (yield 52%).

Aufarbeitung

  1. washthe mixture was washed 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
  4. additionThe resulting crystals were dispersed in diethyl ether
  5. filtrationcollected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-df76d8704cd34a7b8a2a3944fba0c383
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975411B2

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