Diisopropylethylamine → Tert-butyl 3-[2-(4-benzyl-1,4-diazepan-1-yl)-2-oxoethyl]morpholine-4-carboxylate

HRID 530456

Reaktionsgleichung

Reaktionsgleichung von HRID 530456
[C:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[CH2:14][C:15]([OH:17])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:18]([N:25]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:18]([N:25]1[CH2:31][CH2:30][CH2:29][N:28]([C:15](=[O:17])[CH2:14][CH:9]2[CH2:10][O:11][CH2:12][CH2:13][N:8]2[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2283651-Benzyl-1,4-diazepaneHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224876632-(4-((Tert-butoxy)carbonyl)morpholin-3-yl)acetic acid

Produkt 1

HCID 68351750Tert-butyl 3-[2-(4-benzyl-1,4-diazepan-1-yl)-2-oxoethyl]morpholine-4-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-N-Boc-morpholine-3-acetic acid (500 mg, 2.04 mmol) and benzyl homopiperazine (388 mg, 2.04 mmol) were dissolved in DMF (20 mL) and cooled to 0° C. DIPEA (553 mg, 4.28 mmol) and HBTU (773 mg, 2.04 mmol) were added and the reaction mixture was stirred for 2 h. The solvents were removed in vacuo and the residue was partitioned between DCM (100 mL) and water (50 mL). The organic fraction was washed with 1 M aq Na2CO3 (25 mL), brine (25 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase column chromatography to give the title compound (730 mg, 86%) as a light yellow gum. LCMS (ES+): 418.4 [MH]+.

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between DCM (100 mL) and water (50 mL)
  3. washThe organic fraction was washed with 1 M aq Na2CO3 (25 mL), brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6c2f86d28e964b1bbc80c170337c49a1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353086B2

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