Ammonia → (S)-3-(tert-Butoxycarbonyl)amino-1-(1-amino-4-chloro-5-isoquinolinesulfonyl)pyrrolidine

HRID 1962463Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([Cl:28])=[CH:20][N:21]=[C:22](Cl)[C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH3:35]>CN1CCN(C)C1=O.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([Cl:28])=[CH:20][N:21]=[C:22]([NH2:35])[C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of Intermediate 26a (0.20 g), and potassium carbonate (0.31 g) in 1,3-dimethyl-2-imidazolidinone (3 ml, Tokyo Kasei Kogyo) was added with 25% aqueous ammonia (2 ml), and the mixture was stirred at 80° C. for 24 hours in a sealed tube. The reaction mixture was added with saturated brine (30 ml), and extracted 3 times with chloroform (30 ml for each time). The combined organic layer was washed twice with saturated brine (50 ml for each time), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol=9:1) to obtain the title compound (64.4 mg).

Workup

extractionextracted 3 times with chloroform (30 ml for each time)
washThe combined organic layer was washed twice with saturated brine (50 ml for each time), and
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record: ord-4ea1fb41f4174cba8649be98a8248e14
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415372B2

Reaction notes

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