4-Methylmorpholine → HCID 11552805, compound

HRID 2414663Notes

Reaction equation

HRID 2414663 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[CH3:24][C:25]1([CH3:38])[S:30][CH2:29][CH2:28][NH:27][C@H:26]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].CN1CCOCC1>C(Cl)(Cl)Cl.CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:27]2[CH2:28][CH2:29][S:30][C:25]([CH3:24])([CH3:38])[C@@H:26]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 114240934-Hydroxybenzene-1-sulfonyl chlorideHCID 11708267BistrimethylsilylacetamidHCID 12985820HCID 12985820, compound

Product 1

HCID 11552805HCID 11552805, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 20.0 g (0.104 mol) of 4-hydroxybenzenesulfonyl chloride in 200 mL of chloroform was added 28.25 mL (0.114 mol) of bis(trimethylsilyl)acetamide and the reaction was stirred at room temperature for 1 h, after which all of the solids have dissolved. To this mixture was added 20.0 g (0.087 mol) of tert-butyl (3S)-2,2-dimethyl-3-thiomorpholine carboxylate followed by 19.2 mL of 4-methylmorpholine and the reaction was stirred overnight at room temperature. After the addition of 400 mL of methanol to the reaction, the resulting mixture was stirred overnight at room temperature and then concentrated in vacuo. The residue was diluted with ethyl acetate and the organics were washed with water and 5% HCl solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting white solid was washed with ether/hexanes (1:2) and dried in vacuo to give 28.4 g (85%) of tert-butyl (3S)-4-[(4-hydroxyphenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholine carboxylate as a white solid. Electrospray Mass Spec 386.5 (M−H)−.

Workup

  1. dissolutionafter which all of the solids have dissolved
  2. stirringthe reaction was stirred overnight at room temperature
  3. customto the reaction
  4. stirringthe resulting mixture was stirred overnight at room temperature
  5. concentrationconcentrated in vacuo
  6. additionThe residue was diluted with ethyl acetate
  7. washthe organics were washed with water and 5% HCl solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. washThe resulting white solid was washed with ether/hexanes (1:2)
  12. customdried in vacuo

Sources & evidence

ORD record
ord-53896e78c094461b931ce52dbb7d0f11
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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