Morpholine → HCID 22612440, compound

HRID 843697Notes

Reaction equation

HRID 843697 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-173ecffe64a4454eada33c90aa653f86
Source dataset
uspto-grants-2002_04
Patent number
US06380219B1

Reaction notes

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