Benzenesulfonyl chloride → HCID 22149018, compound

HRID 1352232Notes

Reaction equation

HRID 1352232 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:12]2[CH:18]=[CH:17][S:16][C:13]=2[NH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC([O-])(C)C.[K+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:12]2[CH:18]=[CH:17][S:16][C:13]=2[N:14]([S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 22149012HCID 22149012, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22149018HCID 22149018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(t-butoxycarbonyl)-2-(6H-thieno[2,3-b]pyrrol-4-yl)ethylamine (54 mg, 0.2 mmol), phenylsulfonyl chloride (70 mg, 0.22 mmol) and KOt-Bu (0.22 mL 1 M solution in THF, 0.22 mmol) in THF is shaken at ambient temperatures for 8 h and concentrated in vacuo. The resultant residue is dissolved in THF, treated with 4N HCl in dioxane (2 mL) shaken at room temperature for 16 h and concentrated in vacuo. This residue is dissolved in a mixture of DMSO, methanol and water and purified by preparative HPLC1, to afford the title product, [M+H]307, retention time (RT) 1.53 min. 1 Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro-C18, 20 mm×50 mm ID, 5 uM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B:0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in THF
  3. additiontreated with 4N HCl in dioxane (2 mL)
  4. stirringshaken at room temperature for 16 h
  5. concentrationconcentrated in vacuo
  6. dissolutionThis residue is dissolved in a mixture of DMSO, methanol and water
  7. custompurified by preparative HPLC1

Sources & evidence

ORD record
ord-9404775945594e38ae940fa50a3f6d8e
Source dataset
uspto-grants-2007_05
Patent number
US07220756B2

Reaction notes

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