Hydrochloric Acid → HCID 90449886, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([C@@H:17]4[CH2:21][O:20]C(C)(C)[O:18]4)=[O:16])[CH2:11]3)[CH2:9][N:8]([C:24]([NH:26][C:27]3[S:28][C:29]([Cl:32])=[CH:30][N:31]=3)=[O:25])[C:5]2=[CH:6][CH:7]=1.CO.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15](=[O:16])[C@@H:17]([OH:18])[CH2:21][OH:20])[CH2:11]3)[CH2:9][N:8]([C:24]([NH:26][C:27]3[S:28][C:29]([Cl:32])=[CH:30][N:31]=3)=[O:25])[C:5]2=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
5-Chloro-N-(5-chlorothiazol-2-yl)-1′-((S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (116 mg, 0.233 mmol) was dissolved in tetrahydrofuran (1 mL) and methanol (1 mL) Thereafter, a 1 N aqueous solution of hydrochloric acid (1 mL) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred at 50° C. for 20 minutes. Thereafter, the reaction solution was diluted with water, and was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (43.4 mg, 41%) in the form of a colorless amorphous product.
Workup
- extractionwas then extracted with chloroform
- washThe organic layer was washed with brine
- dry with materialwas then dried over anhydrous sodium sulfate
- concentrationfollowed by concentration in vacuo
- customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)
Sources & evidence
- ORD record
- ord-74368e5718754225964d2edba018ec95
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921576B2
Reaction notes
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