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 840195노트

반응식

HRID 840195 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 23938Palladium용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cb73701bb7524c129e9fef26afd4297e
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365612B2

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