HCID 67153303, 화합물 → 2-(3-formyl-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide

HRID 1879473노트

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HRID 1879473 반응식
[CH3:1][C@@H:2]1[C@@H:7]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[N:12]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#N)[CH:20]=2)=[O:10])[CH2:6][C@H:5]2[CH2:27][C@@H:3]1[C:4]2([CH3:29])[CH3:28].O.P(P([O-])([O-])=O)([O-])([O-])=[O:32].[Na+].[Na+].[Na+].[Na+]>N1C=CC=CC=1CC(O)=O.O.[Ni]>[CH3:1][C@@H:2]1[C@@H:7]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[N:12]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:32])[CH:20]=2)=[O:10])[CH2:6][C@H:5]2[CH2:27][C@@H:3]1[C:4]2([CH3:29])[CH3:28]

참가 물질

5

반응물 2

HCID 67153303HCID 67153303, 화합물HCID 131730070HCID 131730070, 화합물

생성물 1

HCID 872885452-(3-formyl-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide수율 49.8%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 69477857Pyridine-acetic acid water용매

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온도
0 °C

실험 절차

To a stirred solution of 2-(3-cyano-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.200 g, 0.48 mmol) in a mixture of pyridine-acetic acid-water (2:1:1; 7.2 mL) was added sodium hypophosphate hydrate (0.400 g, 3.77 mmol) at room temperature. The reaction mixture was cooled to 0° C. and Raney Nickel (0.200 g) was added under an argon atmosphere. After stirring at 0° C. for 10 min, the temperature was raised to 40-45° C. and the reaction mixture was stirred for an additional 2.5 h at the same temperature (with monitoring by silica TLC). The reaction mixture was cooled, filtered through a pad of celite and the residue was washed with methanol (5 mL). The combined filtrates were concentrated to provide the crude material, which was purified by silica gel column chromatography (100-200 mesh) using a gradient of 50-60% ethyl acetate/hexanes to give 2-(3-formyl-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.100 g, 49%).

후처리

  1. temperaturethe temperature was raised to 40-45° C.
  2. stirringthe reaction mixture was stirred for an additional 2.5 h at the same temperature (with monitoring by silica TLC)
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a pad of celite
  5. washthe residue was washed with methanol (5 mL)
  6. concentrationThe combined filtrates were concentrated
  7. customto provide the crude material, which
  8. customwas purified by silica gel column chromatography (100-200 mesh)

출처 및 근거

ORD 기록
ord-de4527d00b954805b749579f14c08f31
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314250B2

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