Sulfuryl chloride → HCID 86640213, compound

HRID 908272Notes

Reaction equation

HRID 908272 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[NH2:6][C:7]1[CH:8]=[C:9]([CH:35]=[CH:36][CH:37]=1)[O:10][CH2:11][C@@H:12]([O:31][C:32](=[O:34])[CH3:33])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH2:15]1>C(Cl)Cl.N1C=CC=CC=1>[C:32]([O:31][C@@H:12]([CH2:13][N:14]1[CH2:15][CH2:16][N:17]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH2:18][CH2:19]1)[CH2:11][O:10][C:9]1[CH:35]=[CH:36][CH:37]=[C:7]([N:6]=[S:1](=[O:3])=[O:2])[CH:8]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 67001334HCID 67001334, compound

Product 1

HCID 86640213HCID 86640213, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suitable sulfonyl chloride is added (1.2 mM) to a solution of (S)-1-(3-aminophenoxy)-2-acetoxy-3-[4-(4-methoxyphenylsulfonyl)piperazin-1-yl)propane (1 mM) in CH2Cl2 (1.2 ml) and pyridine (0.5 ml). The mixture is shaken at room temperature up to the completion of the reaction. It is then diluted with CH2Cl2, and washed with saturated aqueous solution of Na2CO3 and then with water. The organic phase is dried with anhydrous Na2SO4, filtered and the solvent is distilled under vacuum. (S)-2-acetoxy-3-[4-(4-methoxyphenylsulfonyl)piperazin-1-yl]-1-(3-sulfonylaminophenoxy)propane is obtained.

Workup

  1. washwashed with saturated aqueous solution of Na2CO3
  2. dry with materialThe organic phase is dried with anhydrous Na2SO4
  3. filtrationfiltered
  4. distillationthe solvent is distilled under vacuum

Sources & evidence

ORD record
ord-bf633f7ddeac445a84ae298a7f51cb99
Source dataset
uspto-grants-2011_09
Patent number
US08017613B2

Reaction notes

Loading…