Tetrahydrofuran → HCID 10327839, 화합물

HRID 863346노트

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HRID 863346 반응식
O1CCCC1.[CH3:6][N:7]([CH3:29])[C:8]([C@@H:10]1[CH2:14][C@H:13]([SH:15])[CH2:12][N:11]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17])=[O:9].C([N-]C1CCCCC1)(C)C.Br[Mg+].C(N(CC)C(C1C=CC=CC=1S([C:55]1[C@H:56]([CH3:83])[C@@H:57]2[C@@H:74]([C@H:75]([O:77][Si:78]([CH3:81])([CH3:80])[CH3:79])[CH3:76])[C:73](=[O:82])[N:58]2[C:59]=1[C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][C:67]([N+:70]([O-:72])=[O:71])=[CH:66][CH:65]=1)=[O:61])=O)=O)C>C(OCC)(=O)C>[CH3:6][N:7]([CH3:29])[C:8]([C@H:10]1[N:11]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)=[O:17])[CH2:12][C@@H:13]([S:15][C:55]2[C@H:56]([CH3:83])[C@@H:57]3[C@@H:74]([C@H:75]([O:77][Si:78]([CH3:81])([CH3:80])[CH3:79])[CH3:76])[C:73](=[O:82])[N:58]3[C:59]=2[C:60]([O:62][CH2:63][C:64]2[CH:65]=[CH:66][C:67]([N+:70]([O-:72])=[O:71])=[CH:68][CH:69]=2)=[O:61])[CH2:14]1)=[O:9]

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran3회HCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidineHCID 57294913HCID 57294913, 화합물HCID 178456742HCID 178456742, 화합물

생성물 1

HCID 10327839HCID 10327839, 화합물수율 78.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2 ml of a tetrahydrofuran solution containing 68 mg (0.19 mmol) of (2S,4S)-2-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-mercaptopyrrolidine were cooled in an ice bath, and then 0.19 ml (0.19 mmol) of a 1M tetrahydrofuran solution of bromomagnesium N-isopropyl-N-cyclohexylamide were added dropwise over a period of 2 minutes. The mixture was stirred for a further 10 minutes at this temperature, and then 1 ml of a tetrahydrofuran solution containing 100 mg of 4-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 38) was added. The mixture was stirred for a further 15 minutes at this temperature, after which ice water was added. The reaction solution was then diluted with ethyl acetate, washed with an aqueous solution of ammonium chloride then with a saturated aqueous solution of sodium chloride. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 10 g of silica gel, eluted with ethyl acetate, to give 94 mg (yield 78%) of the title compound as a foam-like solid.

후처리

  1. temperaturewere cooled in an ice bath
  2. additionwas added
  3. stirringThe mixture was stirred for a further 15 minutes at this temperature
  4. washwashed with an aqueous solution of ammonium chloride
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 10 g of silica gel
  7. washeluted with ethyl acetate

출처 및 근거

ORD 기록
ord-0d620e75d3bd46e7a83c8a36e9fc1c08
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719275

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