Triethylamine → {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester

HRID 1796999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796999
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)=[O:5].[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:16]([O:23][C:24](=[O:25])[NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([C:34](=[O:35])[NH:2][CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=2)[CH2:30][CH2:29]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3723035Cbz-trans-4-(aminomethyl)cyclohexanecarboxylic acidHCID 133658852-Amino-1-(3-(trifluoromethyl)phenyl)ethan-1-one hydrochloride

Produkt 1

HCID 12154029{4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-Amino-1-(3-trifluoromethyl-phenyl)-ethanone hydrochloride (3.4 g, 0.0144 mol (prepared according to the procedure of Leclerc and Bizec (1980) J. Med. Chem. 23:783–744) and 4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid (4.2 g, 0.0144 mol; for a preparation of this reagent see e.g., Svahn et. al. (1986) J. Med. Chem. 29:448–453) in DMF, Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 6.4 g, 0.0144 mol) was added, followed by triethylamine (4.0 mL, 0.0289 mol). The reaction was stirred overnight and then poured into water to produce a thick precipitate. The solid was collected on a sintered glass funnel and washed consecutively with H2O, 3N HCl (2×), H2O, NaHCO3 solution (2×) and H2O. The filter cake was air dried, added to a 500 mL round bottom flask with toluene and concentrated under reduced pressure. Additional toluene (200 mL) was added and the mixture was concentrated again under reduced pressure to yield {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester as a solid. 1H NMR (DMSO-d6): δ0.8–0.93 (m, 2H), 1.2–1.37 (m, 3H), 1.71 (br s, 4H), 2.14 (t, 1H), 2.84 (br s, 2H), 4.57 (br s, 2H), 4.99 (s, 2H), 7.2–7.38 (m, 5H), 7.77(t, 1H), 8.01 (d, J=8.0 Hz, 1H), 8.14–8.26 (m, 3H). MS 477 (M+H)+

Aufarbeitung

  1. customfor a preparation of this reagent
  2. customto produce a thick precipitate
  3. customThe solid was collected on a sintered glass funnel
  4. washwashed consecutively with H2O, 3N HCl (2×), H2O, NaHCO3 solution (2×) and H2O
  5. customdried
  6. additionadded to a 500 mL round bottom flask with toluene
  7. concentrationconcentrated under reduced pressure
  8. additionAdditional toluene (200 mL) was added
  9. concentrationthe mixture was concentrated again under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9158216d6c9c49c480054346d4bb746c
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034034B2

Notizen zur Reaktion

Wird geladen…