4-Chlorobenzenesulfonyl chloride → trans-Methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate

HRID 1011538Notes

Reaction equation

HRID 1011538 reaction equation
C(O)(=O)C.[NH2:5][C@@H:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[C:13]([O:15][CH3:16])=[O:14].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C>O1CCCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:5][C@@H:6]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[C:13]([O:15][CH3:16])=[O:14])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 66669572trans-Methyl 2-aminocycloheptanecarboxylate acetate

Product 1

HCID 66669620trans-Methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-methyl 2-aminocycloheptanecarboxylate acetate (652 mg, 2.82 mmol), 4-chlorobenzene sulfonyl chloride (893 mg, 4.23 mmol), and triethylamine (1.18 mL, 8.46 mmol) was stirred in 20 mL tetrahydrofuran for 2 h. The reaction was partitioned between 100 mL diethyl ether and 100 mL brine. The organic layer was dried over sodium sulfate, concentrated, and purified by flash chromatography on 40 g silica gel with 15 to 40% ethyl acetate in hexane to yield trans-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (253 mg, 26%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.79 (1H, m), 7.74-7.76 (1H, m), 7.44-7.47 (1H, m), 7.42-7.44 (1H, m), 5.21 (1H, d, J=8.56 Hz), 3.68 (1H, qd, J=8.48, 3.78 Hz), 3.43 (3H, s), 2.44 (1H, td, J=8.56, 3.27 Hz), 1.75-1.82 (1H, m), 1.56-1.73 (4H, m), 1.34-1.54 (5H, m). LC/MS R.T.=2.89 min; [M−H]+=344.04; [M+Na]+=368.16; [M−H]−=344.04.

Workup

  1. customThe reaction was partitioned between 100 mL diethyl ether and 100 mL brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography on 40 g silica gel with 15 to 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ad7ae6c96332435d94e11f48ec29caf3
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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