1-Propanesulfonyl chloride → HCID 66702030, compound

HRID 424656Notes

Reaction equation

HRID 424656 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH2:8]([S:15][C:16]1[N:21]=[C:20]([NH:22]S(C)(=O)=O)[CH:19]=[C:18]([NH:27][C@H:28]([CH3:31])[CH2:29]O)[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:32](N(CC)C(C)C)(C)C>C(Cl)Cl>[CH2:8]([S:15][C:16]1[N:21]=[C:20]([NH:22][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH:19]=[C:18]([NH:27][C@H:28]([CH3:31])[CH2:29][CH3:32])[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 57833159HCID 57833159, compound

Product 1

HCID 66702030HCID 66702030, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Propane-1-sulfonyl chloride (0.14 g) in DCM (1 ml) was added to a solution of the subtitle product of Example 3 step (0.2 g) in DCM (3 ml) and N,N-diisopropylethylamine (0.14 g) at 0° C. The reaction mixture was stirred for 24 h at room temperature. To the reaction mixture more N,N-diisopropylethylamine (0.14 g) was added and the reaction mixture was stirred for an additional 24 h. The DCM was removed under reduced pressure and the residue dissolved in THF (2 ml). To this mixture sodium hydroxide (10%, 2 ml) was added and stirred overnight. The reaction mixture was diluted with EtOAc (50 ml). The organic layer was separated from the aqueous layer and evaporated to dryness. To the residue was added aqueous hydrochloric acid (1M, 30 ml) and THF (10 ml). This was stirred at room temperature for 3 h. The mixture was extracted with EtOAc (2×50 ml). The organics were washed with brine (30 ml). The combined organic layers were dried (MgSO4) and concentrated. This material was purified by reverse phase HPLC (90% to 5% 0.02M ammonium hydroxide/acetonitrile) to yield the title compound as a white solid. Yield: 30 mg.

Workup

  1. customat 0° C
  2. stirringthe reaction mixture was stirred for an additional 24 h
  3. customThe DCM was removed under reduced pressure
  4. dissolutionthe residue dissolved in THF (2 ml)
  5. additionTo this mixture sodium hydroxide (10%, 2 ml) was added
  6. stirringstirred overnight
  7. additionThe reaction mixture was diluted with EtOAc (50 ml)
  8. customThe organic layer was separated from the aqueous layer
  9. customevaporated to dryness
  10. additionTo the residue was added aqueous hydrochloric acid (1M, 30 ml) and THF (10 ml)
  11. stirringThis was stirred at room temperature for 3 h
  12. extractionThe mixture was extracted with EtOAc (2×50 ml)
  13. washThe organics were washed with brine (30 ml)
  14. dry with materialThe combined organic layers were dried (MgSO4)
  15. concentrationconcentrated
  16. customThis material was purified by reverse phase HPLC (90% to 5% 0.02M ammonium hydroxide/acetonitrile)

Sources & evidence

ORD record
ord-4e2781a37b614e4088d05e14bed07595
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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