4-Methylmorpholine → Methyl (3S)-4-{[4-(2,3-butadienyloxy)phenyl]sulfonyl}-2,2-dimethyl-3-thiomorpholinecarboxylate

HRID 1180550Notes

Reaction equation

HRID 1180550 reaction equation
[CH3:1][C:2]1([CH3:12])[S:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]([O:10][CH3:11])=[O:9].CN1CCOCC1.[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH:21]=[C:22]=[CH2:23]>C(Cl)Cl>[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([N:4]2[CH2:5][CH2:6][S:7][C:2]([CH3:12])([CH3:1])[C@@H:3]2[C:8]([O:10][CH3:11])=[O:9])(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH:21]=[C:22]=[CH2:23]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 18345630methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylateHCID 552804204-(2,3-Butadienyloxy)benzenesulfonyl chloride

Product 1

HCID 86588660Methyl (3S)-4-{[4-(2,3-butadienyloxy)phenyl]sulfonyl}-2,2-dimethyl-3-thiomorpholinecarboxylateYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of product from Example 23 (155 mg, 0.82 mmol) in methylene chloride (5 ml) was added N-methylmorpholine (0.180 ml, 1.64 mmol) followed by the product from Example 5 (200 mg, 0.82 mmol). The resulting mixture was stirred for 15 hours at room temperature. The solvent was removed in vacuo and the residue dissolved in ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride and dried over anhydrous sodium sulfate. The crude residue was purified by flash chromatography to give 170 mg (52%) of the product.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-44be6d97419545ad978f46b37b8b0f45
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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