3,5-Dichlorobenzenesulfonyl chloride → 3,5-dichlorophenyl-sulfonyl-L-proline methyl ester

HRID 279720Notes

Reaction equation

HRID 279720 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.[Cl:11][C:12]1[CH:13]=[C:14]([S:19](Cl)(=[O:21])=[O:20])[CH:15]=[C:16]([Cl:18])[CH:17]=1>N1C=CC=CC=1.O>[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[S:19]([C:14]1[CH:13]=[C:12]([Cl:11])[CH:17]=[C:16]([Cl:18])[CH:15]=1)(=[O:21])=[O:20]

Participants

5

Reactant 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 536917753,5-dichlorophenyl-sulfonyl-L-proline methyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

L-Proline methyl ester hydrochloride (2.68 g, 16.2 mmol) was dissolved in pyridine (20 mL), 3,5-dichlorophenylsulfonyl chloride (3.57 g, 14.6 mmol) was added and the mixture was stirred for 19 hr. Water (5 mL) was added and the mixture was stirred for 45 min before diluting with water (200 mL). The mixture was extracted with Et2O (2×150 mL) and the combined extracts were washed with water (3×100 mL), 1N HCl (150 mL) and saturated aq NaHCO3 (150 mL), then dried (MgSO4), filtered and evaporated in vacuo to give 3,5-dichlorophenyl-sulfonyl-L-proline methyl ester as an oil (4.34 g, 88%).

Workup

  1. stirringthe mixture was stirred for 45 min
  2. extractionThe mixture was extracted with Et2O (2×150 mL)
  3. washthe combined extracts were washed with water (3×100 mL), 1N HCl (150 mL) and saturated aq NaHCO3 (150 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-3898278b1cde4db1aff8ec4adee8e4c0
Source dataset
uspto-grants-2002_03
Patent number
US06362341B1

Reaction notes

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