Sodium Bicarbonate → HCID 23521605, compound

HRID 1593513Notes

Reaction equation

HRID 1593513 reaction equation
[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[N:13]([S:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=2)(=[O:30])=[O:29])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

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-f24eb53ef6114a5e94d740d791a5b519
Source dataset
uspto-grants-2007_11
Patent number
US07297705B2

Reaction notes

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