Ammonium Chloride → 5-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-1-benzofuran-2-sulfonamide

HRID 33438Notes

Reaction equation

HRID 33438 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@@H:7]([CH3:16])[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])[C:3]1=[O:17].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[O:26][C:25]([S:27](Cl)(=[O:29])=[O:28])=[CH:24][C:23]=2[CH:31]=1.[Cl-].[NH4+]>C(#N)C.N1C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[O:26][C:25]([S:27]([NH:1][C@H:2]3[CH2:6][CH2:5][N:4]([C@@H:7]([CH3:16])[C:8]([N:10]4[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)=[O:9])[C:3]3=[O:17])(=[O:29])=[O:28])=[CH:24][C:23]=2[CH:31]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 151586095-Chlorobenzofuran-2-sulfonyl Chloride2×HCID 16125562(3S)-3-Amino-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]pyrrolidin-2-one2×

Product 1

HCID 161256165-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-1-benzofuran-2-sulfonamideYield 55.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (3S)-3-amino-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]pyrrolidin-2-one [Intermediate 40] (0.077 g) in anhydrous acetonitrile (2 ml) were added 5-chloro-1-benzofuran-2-sulfonyl chloride [Intermediate 51] (0.043 g) in acetonitrile (2 ml) and pyridine (0.057 ml), and the mixture was stirred at room temperature for 72 h. Saturated ammonium chloride solution (2 ml) was added and the resultant mixture stirred at room temperature for 20 min. The mixture was concentrated under reduced pressure and the residue partitioned between chloroform and hydrochloric acid (2M). The organic layer was washed with saturated sodium bicarbonate and brine. The organic layer was isolated, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (0.043 g) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between chloroform and hydrochloric acid (2M)
  3. washThe organic layer was washed with saturated sodium bicarbonate and brine
  4. customThe organic layer was isolated
  5. dry with materialdried (over magnesium sulphate)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f24b62e620a40aeb07c0739157c8223
Source dataset
uspto-grants-2008_09
Patent number
US07429587B2

Reaction notes

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