Réaction #7410

ord-49ce8660a0d44e569b4a46c3a121a7e7

Équation de réaction

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
Rendement 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

Réactifs

—
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

Réactifs

Aucun

Solvants

C1CCOC1
THF
O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Concentrationconcentrated under reduced pressure
  2. 2
    AutreThe residue was purified
  3. 3
    Lavageeluting with methanol

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07084139B2uspto-grants-2006_08