4-Chlorobenzenesulfonyl chloride → HCID 59679493, compound

HRID 1393215Notes

Reaction equation

HRID 1393215 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:13][CH:12]2[NH:14][CH:8]([CH2:9][C:10](=[O:15])[CH2:11]2)[CH2:7]1)=[O:5])[CH3:2].CCN(CC)CC.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:13][CH:12]2[N:14]([S:30]([C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=3)(=[O:32])=[O:31])[CH:8]([CH2:9][C:10](=[O:15])[CH2:11]2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 59679469HCID 59679469, compound

Product 1

HCID 59679493HCID 59679493, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester (5.91 g, 27.9 mmol) was dissolved in methylene chloride (60 mL). Et3N (7.76 mL, 55.9 mmol) and 4-chlorobenzenesulfonyl chloride (7.08 g, 33.6 mmol) were added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (50 mL) and washed with saturated NaHCO3 (50 mL). The aqueous phase was separated and extracted once with methylene chloride (50 mL). The combined organic phases were then dried (Na2SO4), filtered, concentrated under vacuum and the residue was purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1) to give 9.52 g (88%) of 9-(4-chloro-benzenesulfonyl)-7-oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester. Retention time (min)=2.100, method [1], MS(ESI) 408.1 (M+Na); 1H NMR (300 M Hz, CDCl3) δ 7.81 (d, J=8.2 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 4.61-4.57 (m, 2H), 4.09 (q, J=7.1 Hz, 2H), 2.80 (dd, J=17.0, 7.1 Hz, 2H), 2.67-2.51 (m, 1H), 2.41 (d, J=16.4 Hz, 2H), 1.99-1.90 (m, 2H), 1.80 (dt, J=13.2, 4.4 Hz, 2H), 1.20 (t, J=7.1 Hz, 3H).

Workup

  1. washwashed with saturated NaHCO3 (50 mL)
  2. customThe aqueous phase was separated
  3. extractionextracted once with methylene chloride (50 mL)
  4. dry with materialThe combined organic phases were then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customthe residue was purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1)

Sources & evidence

ORD record
ord-40223c59e3a14d8cb28af8d0b237c9df
Source dataset
uspto-grants-2008_03
Patent number
US07345056B2

Reaction notes

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