Water → HCID 68292273, compound

HRID 339905Notes

Reaction equation

HRID 339905 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Li+].CCC[CH2-].C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][S:22](=[O:36])(=[O:35])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[O:33][CH3:34])=[CH:17][CH:16]=1.O>C1COCC1>[CH3:34][O:33][C:26]1[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:25]=1[CH2:24][NH:23][S:22]([CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:13])=[CH:16][CH:17]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 61028n-Butyl lithiumHCID 68292257HCID 68292257, compound

Product 1

HCID 68292273HCID 68292273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of morpholine (0.69 ml) in THF (10 ml) was added, at −78° C., N-butyllithium (1.6 M, 3.3 ml), and the solution was stirred for 10 min. A solution of 4-[(2,4-dimethoxybenzylsulfamoyl)methyl]benzoic acid methyl ester (1 g) was added and the solution was warmed up to room temperature and stirred for a further 30 minutes. After the addition of water (100 ml), the mixture was extracted with ethyl acetate (2×50 ml). The organic phases were dried over magnesium sulfate and concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (450 mg) with a molecular weight of 434.5 g/mol (C21H26N2O6S).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  2. dry with materialThe organic phases were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThis was followed by purification by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-2c95ea0bbd8e422a8ea586412bbf01ce
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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