반응 #7413

ord-993085dca3ef4537b2715ac868b3332c

반응 방정식

CC=O
acetaldehyde
C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
N-{(3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl }-6-chloronaphthalene-2-sulfonamide
CC(=O)O
acetic acid
CC(=O)O
acetic acid
CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC[N+](CC)(CC)CC
tetraethylammonium triacetoxyborohydride
CC=O
acetaldehyde
CCNC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1
title compound
CCNC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1
6-Chloro-N-((3S)-1-{(1S)-2-[3-(ethylamino)piperidin-1-yl]-1-methyl-2-oxoethyl}-2-oxopyrrolidin-3-yl)naphthalene-2-sulfonamide

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

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

실험 절차

To a solution of acetaldehyde (0.041 ml from a stock solution made up from 0.0127 l 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 (0.005 g). 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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07084139B2uspto-grants-2006_08