2-Aminoheptane → N-(1-Methylhexyl)-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-4,5-dihydroisoxazole-3-carboxamide

HRID 1643519

Reaktionsgleichung

Reaktionsgleichung von HRID 1643519
[F:1][C:2]([F:18])([F:17])[C:3]([CH:9]1[O:13][N:12]=[C:11]([C:14]([OH:16])=O)[CH2:10]1)([OH:8])[C:4]([F:7])([F:6])[F:5].[NH2:19][CH:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:21].CN1CCOCC1.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=O)C.CCOC(C)=O>[CH3:21][CH:20]([NH:19][C:14]([C:11]1[CH2:10][CH:9]([C:3]([OH:8])([C:2]([F:18])([F:1])[F:17])[C:4]([F:5])([F:6])[F:7])[O:13][N:12]=1)=[O:16])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

7

Edukt 4

HCID 56032-AminoheptaneHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11323479HCID 11323479, Verbindung

Produkt 1

HCID 10270978N-(1-Methylhexyl)-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-4,5-dihydroisoxazole-3-carboxamideAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-4,5-dihydroisoxazole-3-carboxylic acid from example 8-2 (84 mg, 0.3 mmol), 2-aminoheptane (69 mg, 0.6 mmol), 4-methylmorpholine (121 mg, 1.2 mmol), and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (265 mg, 0.6 mmol) in DMF (0.5 ml) was stirred at r.t. for 17 h. The reaction mixture was diluted with EtOAc, washed with water, 1 M citric acid and brine, then dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by preparative TLC (EtOAc:Haxanes, 2:1) to afford the title compound as a clear oil (74 mg, 65%). 1H NMR δ 0.86 (t, 3H), 1.16 (d, 3H), 1.27-1.45 (m, 8H), 3.39 (dd, 1H), 3.65 (dd, 1H), 3.99 (m, 1H), 5.11 (t, 1H), 6.36 (d, 1H). ESIMS: m/z 377 (M−H).

Aufarbeitung

  1. washwashed with water, 1 M citric acid and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by preparative TLC (EtOAc:Haxanes, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a6c38236fcec4df5a7249067bbf8ece4
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119819B2

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