Sulfuryl chloride → HCID 86640213, compound

HRID 1804422Notes

Reaction equation

HRID 1804422 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-44b0e93200da4fb4af024ace594b45b5
Source dataset
uspto-grants-2013_01
Patent number
US08354412B2

Reaction notes

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