7-methoxynaphthalene-2-sulfonyl Chloride → HCID 10836138, compound

HRID 619868Notes

Reaction equation

HRID 619868 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[O:13][C:12]([C:14]#[N:15])=[CH:11][CH:10]=2)[C:4]1=[O:16].[CH3:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25]([S:29](Cl)(=[O:31])=[O:30])=[CH:26]2)=[CH:21][CH:20]=1>C(Cl)Cl>[C:14]([C:12]1[O:13][C:9]([CH2:8][N:5]2[CH2:6][CH2:7][C@H:3]([NH:2][S:29]([C:25]3[CH:24]=[CH:23][C:22]4[C:27](=[CH:28][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)[CH:26]=3)(=[O:31])=[O:30])[C:4]2=[O:16])=[CH:10][CH:11]=1)#[N:15]

Participants

4

Reactant 2

HCID 105152667-methoxynaphthalene-2-sulfonyl ChlorideHCID 21845940HCID 21845940, compound

Product 1

HCID 10836138HCID 10836138, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Methoxynaphthalene-2-sulfonic acid [1-(2-cyanofuran-5-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide is prepared as described in EXAMPLE 125, Part C from of 5-(3-amino-2-oxopyrrolidine-1-ylmethyl)furan-2-carbonitrile hydrochloride (1.1 g, 4.55 mmol), and 7-methoxynaphthalene-2-sulfonyl chloride (1.52 g, 5.9 mmol). After 16 hours, the solution is diluted with CH2Cl2. The organic layer is washed with 0.5 N HCl, water and sat NaCl. The organic layer is dried over Na2SO4, filtered and concentrated. The crude product is purified by column chromatography eluting with 10% EtOAc/CH2Cl2 to afford the title compound (0.88 g, 2.07 mmol) as a white solid.

Workup

  1. custom7-Methoxynaphthalene-2-sulfonic acid [1-(2-cyanofuran-5-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide is prepared
  2. washThe organic layer is washed with 0.5 N HCl, water
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography
  7. washeluting with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-6cf1b0fbfa2a4473bf2ee2bbf2de1509
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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