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4-Methylmorpholine → Di-t-butyl [[4-[[N-[3-(1-t-butyloxycarbonylpiperidin-4-yl)propionyl]-N-methylamino]acetyl]-o-phenylene]dioxy]diacetate

HRID 234133
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 234133
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([OH:18])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:20][NH:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[C:27]([O:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:26]=1)=[O:24].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)C1C=CN=CC=1.CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]([N:21]([CH2:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])=[C:27]([O:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:26]=2)=[O:24])[CH3:20])=[O:18])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acidHCID 86750213di-t-butyl [[4-[(N-methylamino)acetyl]-o-phenylene]dioxy]diacetate hydrochloride

Produkt 1

HCID 54497635
Di-t-butyl [[4-[[N-[3-(1-t-butyloxycarbonylpiperidin-4-yl)propionyl]-N-methylamino]acetyl]-o-phenylene]dioxy]diacetate
Ausbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(1-t-butyloxycarbonylpiperidin-4-yl)propionic acid (257 mg), di-t-butyl [[4-[(N-methylamino)acetyl]-o-phenylene]dioxy]diacetate hydrochloride (446 mg), N-methylmorpholine (101 mg), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 442 mg), and a catalytic amount of 4-dimethylaminopyridine were dissolved in 5 ml of dimethylformamide, and the mixture was stirred at room temperature for 3 hours. After ethyl acetate (100 ml) was added to the reaction mixture, the resulting mixture was washed with water. The solvents were removed under reduced pressure. The residual mixture was purified by column chromatography on silica gel to give 285 mg of the title compound from the fraction eluted with n-hexan:ethyl acetate=3:1.

Aufarbeitung

  1. washthe resulting mixture was washed with water
  2. customThe solvents were removed under reduced pressure
  3. customThe residual mixture was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9d96149cb55a44b4b5f60b3d4359b22e
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05594004

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