Ethyl Acetate → ethyl (3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate

HRID 450771Notes

Reaction equation

HRID 450771 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:31].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>C(#N)C.O>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[CH:17]1[CH:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:31])[N:8]1[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[NH:1][S:33]([CH3:32])(=[O:35])=[O:34]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 72303286ethyl (3RS,4RS)-2-[(1SR,2SR)-2-aminocyclohexyl]-3-(2,4-dichlorophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate

Product 1

HCID 68499589ethyl (3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.25 g of ethyl (3RS,4RS)-2-[(1SR,2SR)-2-aminocyclohexyl]-3-(2,4-dichlorophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate in 30 ml of acetonitrile were added 0.75 ml of methanesulfonyl chloride and 1.6 ml of diisopropylethylamine, followed by stirring at room temperature overnight. Ethyl acetate and water were added thereto to carry out a liquid separation operation, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was added with diethyl ether for crystallization, and collected by filtration to obtain 2.02 g of ethyl(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate as a colorless crystal.

Workup

  1. customa liquid separation operation
  2. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. additionThe residue was added with diethyl ether for crystallization
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a0ac51819cca44c1b8df4f33f8106206
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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