4-Chlorobenzenesulfonyl chloride → HCID 59679493, compound

HRID 2061584Notes

Reaction equation

HRID 2061584 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 (4) (5.91 g, 27.9 mmol) was dissolved in CH2Cl2 (60 mL). Et3N (7.76 mL, 55.9 mmol) and 4-chlorobenzenesulfonyl chloride (5) (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 CH2Cl2 (50 mL) and washed with saturated NaHCO3 (50 mL). The aqueous phase was separated and extracted once with CH2Cl2 (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 (6). Retention time (min)=2.100, method [1], MS (ESI) 408.1 (M+Na); 1H NMR (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 CH2Cl2 (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-5a0c3f1767cf46d68f511da5bfcf311c
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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