Dimethylformamide → N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine

HRID 2923

Reaktionsgleichung

Reaktionsgleichung von HRID 2923
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O.Cl.[CH3:46][O:47][C:48]1[CH:54]=[C:53]([CH3:55])[CH:52]=[C:51]([O:56][CH3:57])[C:49]=1[NH2:50]>C(OC(C)C)(C)C.C(OCC)(=O)C.C(N(CC)CC)C>[C:4]([O:3][C:1]([NH:8][CH2:9][C:10](=[O:12])[NH:50][C:49]1[C:51]([O:56][CH3:57])=[CH:52][C:53]([CH3:55])=[CH:54][C:48]=1[O:47][CH3:46])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 189364892,6-Dimethoxy-4-methylaniline hydrochloride

Produkt 1

HCID 18936465N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7914Diisopropyl EtherLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6.6 g of N-Boc-glycine and 15.6 g of BOP are successively added to 100 ml of dimethylformamide and then, at 0° C., 14 ml of triethylamine are added dropwise. The mixture is left for 20 minutes at 0° C. and 6.7 g of 2,6-dimethoxy-4-methylaniline hydrochloride are then added portionwise. The reaction mixture is left at room temperature for 15 hours. 400 ml of ethyl acetate are added to the reaction mixture and the organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution and then with water. The organic phase is dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a semi-crystalline residue which is solidified in diisopropyl ether to provide N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine, in the form of white crystals; M.p.=146° C.; Yield: 96%.

Aufarbeitung

  1. waitThe reaction mixture is left at room temperature for 15 hours
  2. washthe organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution
  3. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  4. customEvaporation of the solvent
  5. customleaves a semi-crystalline residue which

Quellen und Nachweise

ORD-Eintrag
ord-9cb77feee68640b1aefc6e6668171bff
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731340

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