Tetrahydrofuran → HCID 10327839、化合物

HRID 863346ノート

反応式

HRID 863346 の反応式
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]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran3 回HCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidineHCID 57294913HCID 57294913、化合物HCID 178456742HCID 178456742、化合物

生成物 1

HCID 10327839HCID 10327839、化合物収率 78.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0d620e75d3bd46e7a83c8a36e9fc1c08
出典データセット
uspto-grants-1998_02
特許番号
US05719275

反応ノート

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