Water → HCID 68291906, compound

HRID 339912Notes

Reaction equation

HRID 339912 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=O)=[CH:13][CH:12]=1)(=[O:9])=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][NH:6][S:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:15][CH:16]=1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68359256HCID 68359256, compound

Product 1

HCID 68291906HCID 68291906, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2,4-dimethoxybenzyl)-C-[4-(2-morpholin-4-yl-2-oxoethyl)phenyl]methanesulfonamide (313 mg) in THF (10 ml) was added, at 0° C., lithium aluminum hydride (66 mg) in portions, and the mixture was stirred at room temperature for 1 h. Then water (0.4 ml), 6 M NaOH (0.3 ml) and water again (1.2 ml) were added successively. The solids were filtered off and dichloromethane was added to the filtrate. The organic phase was removed, dried over magnesium sulfate and concentrated. The crude product was purified by means of preparative HPLC. This gave the product (57 mg) with a molecular weight of 434.6 g/mol (C22H30N2O5S).

Workup

  1. filtrationThe solids were filtered off
  2. additiondichloromethane was added to the filtrate
  3. customThe organic phase was removed
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-fe9b33bedbed4ac4b5e5effaa075eb4c
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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