Hydrochloric Acid → N-[(6-Chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycine

HRID 2110064Notes

Reaction equation

HRID 2110064 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]([C@H:21]1[CH2:25][CH2:24][N:23]([C@@H:26]([CH3:35])[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])[C:22]1=[O:36])[CH2:16][C:17]([O:19]C)=[O:18])(=[O:14])=[O:13])[CH:6]=[CH:5]2.[OH-].[Li+].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]([C@H:21]1[CH2:25][CH2:24][N:23]([C@@H:26]([CH3:35])[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])[C:22]1=[O:36])[CH2:16][C:17]([OH:19])=[O:18])(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10187090HCID 10187090, compound

Product 1

HCID 10142920N-[(6-Chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycineYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 [Example 55] (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.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified

Sources & evidence

ORD record
ord-de2500cce49a4cd08d4001f25285dc91
Source dataset
uspto-grants-2009_04
Patent number
US07517879B2

Reaction notes

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