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

HRID 2425418Notes

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-af2fc6f0be824862b614c4e00e3792cd
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964613B2

Reaction notes

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