Water → HCID 86645198, compound

HRID 1747054Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[N:15]1[CH:24]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[CH:23]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:38])(=[O:7])=[O:6].[H-].[Na+].C(OCC)(=O)C.O>C1COCC1>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[CH:24]1[CH:23]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH2:21]2)[C:16](=[O:38])[N:15]1[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[N:8]1[CH2:2][CH2:3][CH2:4][S:5]1(=[O:6])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1.63 g of ethyl(3RS,4RS)-2-[(1SR,2SR)-2-{[(3-chloropropyl)sulfonyl]amino}cyclohexyl]-3-(2,4-dichlorophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate in 20 ml of THF was added 142 mg of sodium hydride, followed by stirring at 50° C. overnight. Ethyl acetate and water were added thereto to carry out a liquid separation operation. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 466 mg of ethyl(3RS,4RS)-3-(2,4-dichlorophenyl)-2-[(1SR,2SR)-2-(1,1-dioxidoisothiazolidin-2-yl)cyclohexyl]-1-oxo-tetrahydroisoquinoline-4-carboxylate as a colorless crystal.

Workup

customa liquid separation operation
washThe organic layer was washed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record: ord-45cac1b605d740729b80286309f63c22
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150541B2

Reaction notes

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