Acetic Acid → 6-Chloro-N-((3S)-1-{(1S)-2-[3-(ethylamino)piperidin-1-yl]-1-methyl-2-oxoethyl}-2-oxopyrrolidin-3-yl)naphthalene-2-sulfonamide

HRID 1765667

Reaktionsgleichung

Reaktionsgleichung von HRID 1765667
[CH:1](=O)[CH3:2].C(O)(=O)C.[NH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:39])[C@@H:16]([N:18]2[CH2:22][CH2:21][C@H:20]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[C:32]([Cl:37])[CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:19]2=[O:38])[CH3:17])[CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C([N+](CC)(CC)CC)C>C(Cl)Cl>[Cl:37][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([S:24]([NH:23][C@H:20]1[CH2:21][CH2:22][N:18]([C@@H:16]([CH3:17])[C:15]([N:11]3[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][CH2:1][CH3:2])[CH2:10]3)=[O:39])[C:19]1=[O:38])(=[O:26])=[O:25])[CH:36]=[CH:35]2

Komponenten

6

Edukt 4

HCID 176Acetic Acid2×HCID 177Acetaldehyde2×HCID 69329851N-((3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl)-6-chloronaphthalene-2-sulfonamideHCID 131725882Tetraethylammonium triacetoxyborohydride

Produkt 1

HCID 693295886-Chloro-N-((3S)-1-{(1S)-2-[3-(ethylamino)piperidin-1-yl]-1-methyl-2-oxoethyl}-2-oxopyrrolidin-3-yl)naphthalene-2-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

To a solution of acetaldehyde (0.041 ml from a stock solution made up from 0.01271 acetaldehyde dissolved in 1 ml DCM)) in dry DCM (0.4 ml) treated with acetic acid (0.1 ml from a stock solution made up from 0.0054 ml acetic acid dissolved in 1 ml DCM) was added N-{(3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-6-chloronaphthalene-2-sulfonamide [Example 365] (0.045 g) followed by tetraethylammonium triacetoxyborohydride (0.0059 ). The mixture was stirred at room temperature, under nitrogen, for 60 h. DCM (1 ml) was added and the resultant solution washed with saturated sodium bicarbonate (1 ml) in a hydrophobic frit. The solvent was concentrated under reduced pressure and the residue purified by mass directed preparative h.p.l.c. to give the title compound (0.8 mg) as an oil.

Aufarbeitung

  1. washthe resultant solution washed with saturated sodium bicarbonate (1 ml) in a hydrophobic frit
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customthe residue purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-667c5f55cc8e4b4f8b64e011fe6d6a7b
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226929B2

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