Water → HCID 69309281, compound

HRID 1394055Notes

Reaction equation

HRID 1394055 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@@H:13]([NH2:17])[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[S:38][C:37]([S:39](Cl)(=[O:41])=[O:40])=[CH:36][CH:35]=1.O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][C@@H:13]([NH:17][S:39]([C:37]2[S:38][C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)=[CH:35][CH:36]=2)(=[O:40])=[O:41])[CH:14]([CH3:15])[CH3:16])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 69312023HCID 69312023, compound

Product 1

HCID 69309281HCID 69309281, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The product of Example 7, Step (c) (0.050 g) was dissolved in acetone (1 ml). K2CO3 [0.033 g dissolved in H2O (0.5 ml)] was then added, followed by 5-pyridin-2-yl-thiophene-2-sulfonyl chloride (0.041 g) and the reaction left to stir for 1 hr. Water was then added and the product extracted with ethyl acetate. The combined organic extracts dried, filtered and concentrated. Purification by flash silica column chromatography with 30% EtOAc/68% Hexane/2% TEA as eluent, and then reverse phase HPLC [(50% MeCN/NH4OAcaq (0.1%)] gave the title compound as a solid (0.023 g).

Workup

  1. waitthe reaction left
  2. extractionthe product extracted with ethyl acetate
  3. customThe combined organic extracts dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica column chromatography with 30% EtOAc/68% Hexane/2% TEA as eluent

Sources & evidence

ORD record
ord-4031213b43c741869d9414739eace71f
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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