Diisopropylamine → HCID 59784103, Verbindung

HRID 2079771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079771
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21]([OH:23])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.[C@H:31]1([NH2:41])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21](=[O:23])[NH:41][C@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH2:32]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 7912DiisopropylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70580721-Aminotetralin, (R)-HCID 407870284-Benzyl-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Produkt 1

HCID 59784103HCID 59784103, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Anhydrous DMF (20 ml) is added to a 100 ml round bottom flask containing compound 4 (325 mg, 1.014 mmol) under N2. After ten minutes diisopropylamine (0.88 ml, 5.07 mmol) is added to the flask. It is then stirred at room temperature for 1.5 hrs. (R)-1,2,3,4-Tetrahydro-1-napthylamine (149.3 mg, 1.014 mmol) is then added to the flask and stirred for 1 hr. HBTU (423.07 mg, 1.115 mmol) is added to the reaction followed by HOBT (152.1 mg, 1.126 mmol). The reaction mixture is then stirred at room temperature under N2 overnight at which point LCMS shows completion of the reaction. It is then diluted with EtOAc and washed subsequently with 1.0 M citric acid, brine, saturated sodiumbicarbonate, brine, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound is flash column purified using hexane and ethylacetate gradient solvent system to yield 423 mg (93%) of the desired product 6. HPLC shows this compound to be greater than 99% pure.

Aufarbeitung

  1. stirringstirred for 1 hr
  2. stirringThe reaction mixture is then stirred at room temperature under N2 overnight at which point LCMS
  3. customcompletion of the reaction
  4. washwashed subsequently with 1.0 M citric acid, brine, saturated sodiumbicarbonate, brine, water and brine
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-82917f57047745038c2bd7cb54627d31
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932255B2

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