Morpholine → HCID 22612440, compound

HRID 1857365Notes

Reaction equation

HRID 1857365 reaction equation
[C:1]([CH2:4][N:5]([CH2:17][C:18]([OH:20])=[O:19])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7])([OH:3])=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C(OC(=O)C)(=O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([N:5]([CH2:17][C:18]([OH:20])=[O:19])[CH2:4][C:1]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:3])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 705729HCID 705729, compound

Product 1

HCID 22612440HCID 22612440, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

[Carboxymethyl(4-methoxybenzenesulfonyl)amino]acetic acid (0.5 grams, 1.65 mmol) in acetic anhydride (15 mL) was dissolved in acetic anhydride by gentle warming. The resulting solution was stirred at room temperature overnight. The acetic anhydride was removed by evaporation under vacuum; the residue was dissolved in methylene chloride and morpholine (0.16 mL, 1.82 mmol) was added. The mixture was stirred overnight at room temperature and then concentrated under vacuum. The residue was dissolved in ethyl acetate, washed with 1N hydrochloric acid solution, water and brine, dried over magnesium sulfate and concentrated to afford [(4-methoxybenzenesulfonyl)(2-morpholin-4-yl-2-oxoethyl)amino]acetic acid as an oil, 0.33 grams (54%).

Workup

  1. customThe acetic anhydride was removed by evaporation under vacuum
  2. dissolutionthe residue was dissolved in methylene chloride
  3. stirringThe mixture was stirred overnight at room temperature
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 1N hydrochloric acid solution, water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-24698cbd4b5e4e30b659980c78ca5f0e
Source dataset
uspto-grants-2000_11
Patent number
US06147074

Reaction notes

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