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

HRID 421187Notes

Reaction equation

HRID 421187 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 30 min. 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-0a2b3a4aec5a409aa16da4c6b55b69f3
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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