Triethylamine → [1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester

HRID 1443631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443631
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:12](=[O:29])[NH:13][C:14]1[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH2:31](N(CC)CC)C.C(N[C@@H](C(O)=O)C(C)C)(OC(C)(C)C)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:12](=[O:29])[NH:13][C:14]1[CH:19]=[C:18]([CH3:31])[CH:17]=[CH:16][C:15]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68558928[1-(2-Benzylamino-5-bromo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 66886932[1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of [1-(2-benzylamino-5-bromo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (250 mg, 0.9 mmol) and triethylamine (0.19 ml, 1.35 mmol) in dry DMF (5 ml), was added Boc-D-valine (290 mg, 1.35 mmol) followed by TBTU (290 mg, 0.9 mmol,). The reaction mixture was stirred at room temperature overnight. Ethyl acetate was added. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered, and the filtrated was concentrated in vacuo. The crude material was purified by flash chromatography to yield [1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester.

Aufarbeitung

  1. washThe organic layer was washed with saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrated was concentrated in vacuo
  5. customThe crude material was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a3720bfb3d094bc0bbe0aeacbd661c38
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662581B1

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