Reaktion #7410

ord-49ce8660a0d44e569b4a46c3a121a7e7

Reaktionsgleichung

COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1
methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}glycinate
[Li+].[OH-]
lithium hydroxide
Cl
hydrochloric acid
→
CO.Cl
HCl methanol
Ausbeute 10.0%
C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
title compound
C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
N-[(6-Chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}glycine

Edukte

—
resultant solution
COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1
methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}glycinate
[Li+].[OH-]
lithium hydroxide
Cl
hydrochloric acid

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated under reduced pressure
  2. 2
    SonstigeThe residue was purified
  3. 3
    Wascheneluting with methanol

Vorschrift

To a solution of methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}glycinate (0.010 g) in THF (1 ml) was added lithium hydroxide (0.005 g) in water (1 ml), and the resultant solution stirred for 16 h. The mixture was acidified to pH5 using hydrochloric acid (2N), and then concentrated under reduced pressure. The residue was purified using SPE (eluting with methanol and then 10% HCl/methanol) to give the title compound (0.01 g) as a white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084139B2uspto-grants-2006_08