Sodium ethoxide → (S)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1-ethoxy-4-chloro-5-isoquinolinesulfonyl)pyrrolidine

HRID 2425435Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH:10]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[C:19]3[C:20]([Cl:29])=[CH:21][N:22]=[C:23](Cl)[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:17])=[O:16])[CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-:30][CH2:31][CH3:32].[Na+]>C(O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]([C@H:10]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[C:19]3[C:20]([Cl:29])=[CH:21][N:22]=[C:23]([O:30][CH2:31][CH3:32])[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:16])=[O:17])[CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of Intermediate 25 (230 mg) obtained in Example 36-1 in ethanol (10 ml) was added with sodium ethoxide (204 mg, Aldrich), and the mixture was stirred at 50° C. for 12 hours. The reaction mixture was added with saturated brine (10 ml), and extracted three times with ethyl acetate (10 ml for each time), and the combined organic layer was washed with saturated brine (20 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (223 mg).

Workup

extractionextracted three times with ethyl acetate (10 ml for each time), and the combined organic layer
washwas washed with saturated brine (20 ml)
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-13d0baca8f6a43618322a310eb3a142d
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964613B2

Reaction notes

Loading…