Sodium Thiosulfate → HCID 58959848, compound

HRID 915891Notes

Reaction equation

HRID 915891 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.[N:12]1([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]2)=[O:19])[CH2:17][CH2:16]S[CH2:14][CH2:13]1.[S:34]([O-:38])([O-])(=[O:36])=S.[Na+].[Na+]>C(Cl)Cl>[O:36]=[S:34]1(=[O:38])[CH2:14][CH2:13][N:12]([C:18]([N:20]2[CH2:21][CH2:22][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH2:24][CH2:25]2)=[O:19])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 58959852HCID 58959852, compound

Product 1

HCID 58959848HCID 58959848, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g of m-chloroperbenzoic acid was added to 1.0 g of tert-butyl [1-(thiomorpholine-4-carbonyl)piperidin-4-yl]carbamate in 10 ml of methylene chloride under cooling with ice-water bath. The reaction mixture was allowed to room temperature, and stirred for 18 hours. Aqueous saturated sodium thiosulfate solution was added to the reaction mixture, and this was extracted with EtOAc. The organic layer was washed with aqueous saturated sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting solid was washed with diisopropyl ether to obtain 607 mg of tert-butyl [1-(1,1-dioxothiomorpholine-4-carbonyl)piperidin-4-yl]carbamate.

Workup

  1. temperatureunder cooling with ice-water bath
  2. customwas allowed to room temperature
  3. extractionthis was extracted with EtOAc
  4. washThe organic layer was washed with aqueous saturated sodium hydrogencarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. washThe resulting solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-65d1c81d773f4a10bcd9f6df1d383593
Source dataset
uspto-grants-2007_09
Patent number
US07268150B2

Reaction notes

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