Benzenesulfonyl chloride, 2,4-dimethyl- → 8-(2,4-Dimethyl-benzenesulfonyl)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester

HRID 2174973Notes

Reaction equation

HRID 2174973 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([NH:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[S:24](Cl)(=[O:26])=[O:25].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([S:24]([C:18]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=3[CH3:16])(=[O:26])=[O:25])[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 69109Benzenesulfonyl chloride, 2,4-dimethyl-HCID 81531DiisopropylethylamineHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate

Product 1

HCID 670865848-(2,4-Dimethyl-benzenesulfonyl)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,8-Diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (240 mg, 1.1 mmol), 2,4-dimethyl-benzenesulfonyl chloride (278 mg, 1.4 mmol) and di-isopropylethylamine (0.4 mL, 2.3 mmol) were dissolved into DCM (5.0 mL) and stirred at room temperature for 18 h. The reaction mixture was diluted with DCM (25 mL) and washed with 1N NaOH (10 mL) and water (2×20 mL). The organic layers were combined, dried, filtered and concentrated to yield the title compound (300 mg, 97%).

Workup

  1. washwashed with 1N NaOH (10 mL) and water (2×20 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b21014671df4ee7a6bb8cd03e83193c
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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