Sodium Bicarbonate → HCID 23521605, compound

HRID 731603Notes

Reaction equation

HRID 731603 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1.CC(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:28]([N:13]2[C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:19]3[C:11]([CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[CH:12]2)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 22662984HCID 22662984, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23521605HCID 23521605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Boc-6-azatryptamine (1.1 eq.) and 3-methoxybenzenesulfonyl chloride (1.0 eq.) in THF at room temperature is treated portionwise with solid potassium t-butoxide (1.2 eq), stirred at room temperature for 16 h, poured into saturated NaHCO3 and extracted with EtOAc. The combined extracts are dried over MgSO4 and concentrated in vacuo. Chromatographic purification of this concentrate using silica gel and EtOAc/Hexanes as eluent gives the title sulfonated compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customChromatographic purification of this concentrate
  5. customgives the title sulfonated compound

Sources & evidence

ORD record
ord-723a3cc5a8c24285baa56d17b8ed99f6
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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