Réaction #7405

ord-c3726134f7ce47758660d338cb2302ac

Équation de réaction

Cl
hydrochloric acid
COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1
methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycinate
[Li+].[OH-]
lithium hydroxide
→
C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
title compound
Rendement 61.6%
C[C@@H](C(=O)N1CCOCC1)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-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycine
Rendement 61.6%

Réactifs

Cl
hydrochloric acid
COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1
methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycinate
[Li+].[OH-]
lithium hydroxide
—
resultant solution

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

Mode opératoire

To a solution of methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycinate (0.010 g) in THF (2 ml) was added lithium hydroxide (0.003 g) in water (2 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 mass directed preparative h.p.l.c. to give the title compound (0.006 g) as a white solid.

Source

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