Trifluoroacetic acid → Hexahydropyrazino[2,1-c][1,4]thiazin-9(6H)-one 2,2-dioxide

HRID 2245403Notes

Reaction equation

HRID 2245403 reaction equation
CC(OC([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[CH2:13][CH:12]1[C:19]([O:21]C)=O)=O)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:13]1[CH:12]2[C:19](=[O:21])[NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][S:14]1(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59215870Methyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-thiomorpholinecarboxylate 1,1-dioxide

Product 1

HCID 59215885Hexahydropyrazino[2,1-c][1,4]thiazin-9(6H)-one 2,2-dioxideYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-thiomorpholinecarboxylate 1,1-dioxide (D17; 295 mg, 0.88 mmol) in 3 ml of anhydrous dichloromethane was added 1 ml of trifluoroacetic acid and the resulting solution was stirred at room temperature under nitrogen for 1 h 30min. The solvent was removed under reduced pressure and the residue loaded on a SCX column, washed with methanol and eluted with methanolic ammonia. The product was purified further by chromatography (silica cartridge, cyclohexane to ethyl acetate, then dichloromethane to dichloromethane: methanol 70:30) to give 165 mg of the target compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with methanol
  3. washeluted with methanolic ammonia
  4. customThe product was purified further by chromatography (silica cartridge, cyclohexane to ethyl acetate

Sources & evidence

ORD record
ord-b243d316c58f465ab677440898b8ed31
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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