Sodium Hydroxide → HCID 57826939, compound

HRID 422586Notes

Reaction equation

HRID 422586 reaction equation
C(O[K])(C)(C)C.[S:7]1[C:14]2[C:13]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][NH:11][C:10]=2[CH:9]=[CH:8]1.[CH:21]1([S:24](Cl)(=[O:26])=[O:25])[CH2:23][CH2:22]1.[OH-].[Na+]>C1COCC1>[CH:21]1([S:24]([N:11]2[CH:12]=[C:13]([CH2:15][C:16]([OH:18])=[O:17])[C:14]3[S:7][CH:8]=[CH:9][C:10]2=3)(=[O:26])=[O:25])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2760919Cyclopropanesulfonyl chlorideHCID 57826937HCID 57826937, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 57826939HCID 57826939, compoundYield 3.11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tBuOK (0.1 mL, 1.2 equiv, 1.0 M in THF) was added to a solution of ethyl 2-(4H-thieno[3,2-b]pyrrol-6-yl)acetate (0.024 g, 0.11 mmol, 1.0 equiv.) in THF (0.5 mL) in a 20 mL vial. This vial was capped and shaken at room temperature for 10 min. To the mixture a solution of cyclopropanesulfonyl chloride (0.7 mL, 1.2 equiv, 0.2 M in THF) was added and the reaction was shaken at room temperature for 4 h. After which time NaOH (aqueous) (1.0 mL, 1.0 M, 9.5 equiv) was added and the reaction was shaken at room temperature overnight. The crude reaction mixture was then concentrated to dryness under reduced pressure and taken up in 1.5 mL 1:1 DMSO/MeOH and purified by reverse phase HPLC (Table 1, Method h) to give the title compound (0.001 g, 3.11%): LC/MS (Table 1, Method e) Rt=1.29 min; MS m/z 285.9 (M+H)+.

Workup

  1. customThis vial was capped
  2. stirringthe reaction was shaken at room temperature for 4 h
  3. stirringthe reaction was shaken at room temperature overnight
  4. customThe crude reaction mixture
  5. concentrationwas then concentrated to dryness under reduced pressure
  6. custompurified by reverse phase HPLC (Table 1, Method h)

Sources & evidence

ORD record
ord-6122bfc505b947a3b209ab87af9eff04
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

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