4-Methoxybenzenesulfonyl chloride → HCID 86586948, compound

HRID 1167270Notes

Reaction equation

HRID 1167270 reaction equation
[CH2:1]([C@H:8]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:9]([OH:22])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=1>ClCCl>[CH2:1]([C@H:8]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@@H:9]([OH:22])[CH:10]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)[S:48]([C:45]1[CH:44]=[CH:43][C:42]([O:41][CH3:40])=[CH:47][CH:46]=1)(=[O:50])=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59815759HCID 59815759, compound

Product 1

HCID 86586948HCID 86586948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Step 2 (0.63 g, 149 mmol) in anhydrous dichloromethane (7 mL) at 0° C. was added N-ethyldiisopropylamine (0.38 g, 0.51 mL, 2.98 mmol) and a solution of 4-methoxybenzenesulfonyl chloride (0.32 g, 1.56 mmol) in anhydrous dichloromethane (2 mL) and the mixture was stirred at ambient temperature under nitrogen atmosphere for 18 hours. The mixture was washed sequentially with 1M hydrochloric acid, sodium bicarbonate/water, brine, dried (sodium sulfate) and concentrated. The residue was chromatographed (silica gel, dichloromethane/methanol, 97:3) to provide the title compound as a thick oil.

Workup

  1. washThe mixture was washed sequentially with 1M hydrochloric acid, sodium bicarbonate/water, brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe residue was chromatographed (silica gel, dichloromethane/methanol, 97:3)

Sources & evidence

ORD record
ord-67468a6bd21b4261944ee9951cb9d9b7
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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