4-Methylmorpholine → HCID 21997030, compound

HRID 1978217Notes

Reaction equation

HRID 1978217 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH:12]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:13](O)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[OH:28][N:29]1C2C=CC=CC=2N=N1.Cl.NO.CN1CCOCC1>CN(C)C=O>[OH:28][NH:29][C:13](=[O:14])[CH:12]([CH2:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 443297Hydroxyamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21997038HCID 21997038, compound

Product 1

HCID 21997030HCID 21997030, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-chlorobenzenesulfonylmethyl)-3-(4-chlorobenzenesulfonyl)-propionic acid (0.52 g, 1.1 mmol), 1-hydroxybenzotriazole hydrate (0.16 g, 1.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiinde hydrochloride (0.25 g, 1.3 mmol), and hydroxylamine hydrochloride (0.083 g, 1.2 mmol) is stirred in an ice bath for 20 minutes and 4-methylmorpholine (0.28 mL, 2.5 mmol) in dimethylformamide (10 mL) is added. After stirring overnight at ambient temperature, the mixture is partitioned between ethyl acetate and aqueous 10% hydrochloric acid. The organic phase is further extracted with aqueous acid, aqueous sodium bicarbonate, brine, dried over anhydrous sodium sulfate, concentrated in vacuo. The concentrate is chromatographed over silica gel (230-400 mesh) with chloroform/acetone/acetic acid (79/20/1) and the eluate concentrated in vacuo, to yield the title compound as a white solid.

Workup

  1. stirringAfter stirring overnight at ambient temperature
  2. customthe mixture is partitioned between ethyl acetate and aqueous 10% hydrochloric acid
  3. extractionThe organic phase is further extracted with aqueous acid, aqueous sodium bicarbonate, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe concentrate is chromatographed over silica gel (230-400 mesh) with chloroform/acetone/acetic acid (79/20/1)
  7. concentrationthe eluate concentrated in vacuo

Sources & evidence

ORD record
ord-ce7c29b04cf14674aec57af052de30af
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

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