Ethyl Acetate → N-{(2R)-2-hydroxy-3-[(1-methyl-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl)amino]propyl}acetamide

HRID 840195Notes

Reaction equation

HRID 840195 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[CH2:4][S:3]1(=[O:15])=[O:14].CCOC(C)=O.[O:22]1[CH2:24][C@@H:23]1[CH2:25][NH:26][C:27](=[O:29])[CH3:28].FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O>[Pd].CC#N>[OH:22][C@H:23]([CH2:24][NH:11][C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[S:3](=[O:15])(=[O:14])[CH2:4][C:5]=2[CH:10]=1)[CH2:25][NH:26][C:27](=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2734125Magnesium trifluoromethanesulfonateHCID 11051615Acetamide, N-[(2S)-oxiranylmethyl]-HCID 155387111-Methyl-5-nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

Product 1

HCID 15538712N-{(2R)-2-hydroxy-3-[(1-methyl-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl)amino]propyl}acetamideYield 83.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 23938PalladiumSolvent

Procedure

The product of Step 1 (0.20 g, 0.88 mmol) is dissolved into EtOAc (30 mL) in a Parr bottle and 10% Pd/C (100 mg) added under nitrogen. The mixture is hydrogenated on a Parr apparatus for 2 hrs at 30 psi. Filtration and evaporation of solvent gave a white solid. This material is added to a mixture of N-[(2S)oxiranylmethyl] acetamide (0.81 g, 7.0 mmol) and magnesium trifluoromethanesulfonate (0.42 g, 1.3 mmol) in dry CH3CN (10 mL) at room temperature. After 20 hrs solvent is evaporated and the residue purified by chromatography (4%MeOH/CH2Cl2) to give a foamy solid (0.23 g, 79%). HRMS (FAB) calcd for C13H19N3O4S +H1 314.1174, found 314.1174.

Workup

  1. additionadded under nitrogen
  2. filtrationFiltration and evaporation of solvent
  3. customgave a white solid
  4. customAfter 20 hrs solvent is evaporated
  5. customthe residue purified by chromatography (4%MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cb73701bb7524c129e9fef26afd4297e
Source dataset
uspto-grants-2002_04
Patent number
US06365612B2

Reaction notes

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