Hydrochloric Acid → (R,E)-methyl 4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-4-oxobut-2-enoate

HRID 926914

Reaktionsgleichung

Reaktionsgleichung von HRID 926914
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:13])/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10].[CH2:14]1[C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])[S:17][S:16][CH2:15]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CC#N.CCOC(C)=O>[S:16]1[CH2:15][CH2:14][C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:13])/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])=[O:24])[S:17]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6112Lipoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86655426(E)-methyl 4-(2-aminoethylamino)-4-oxobut-2-enoate

Produkt 1

HCID 87351952(R,E)-methyl 4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-4-oxobut-2-enoateAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The HCl salt of (E)-methyl 4-(2-aminoethylamino)-4-oxobut-2-enoate (0.515 mmol) was taken up in 10 mL of CH3CN along with R-lipoic acid (TCI, 106 mg, 0.515 mmol), HATU (215 mg, 0.567 mmol) and DIEA (270 μl, 1.55 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and diluted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gel cinematography (95% CH2Cl2, 5% MeOH) afforded 120 mg of (R,E)-methyl 4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-4-oxobut-2-enoate. MS (EI) calcd for C15H24N2O4S: 360.12; found 361 (M+1).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel cinematography (95% CH2Cl2, 5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-6dfc1d3029a84287b08b420f140d494c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09289503B2

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