Tetrahydrofuran → HCID 10440416、化合物

HRID 1490351

反応式

HRID 1490351 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(CC)C(C1C=CC=CC=1S([C:43]1[C@H:44]([CH3:74])[C@@H:45]2[C@@H:62]([C@H:63]([O:65][Si:66]([C:69]([CH3:72])([CH3:71])[CH3:70])([CH3:68])[CH3:67])[CH3:64])[C:61](=[O:73])[N:46]2[C:47]=1[C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=1)=[O:49])=O)=O)C.[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:6][N:7]([CH3:29])[C:8]([C@@H:10]1[CH2:14][C@H:13]([S:15][C:43]2[C@H:44]([CH3:74])[C@@H:45]3[C@@H:62]([C@H:63]([O:65][Si:66]([C:69]([CH3:72])([CH3:71])[CH3:70])([CH3:67])[CH3:68])[CH3:64])[C:61](=[O:73])[N:46]3[C:47]=2[C:48]([O:50][CH2:51][C:52]2[CH:53]=[CH:54][C:55]([N+:58]([O-:60])=[O:59])=[CH:56][CH:57]=2)=[O:49])[CH2:12][N:11]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)=[O:17])=[O:9]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidineHCID 110288304-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 10440416HCID 10440416、化合物収率 74%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

75 μl of a hexane solution containing 1.6M of butyllithium was added to 1 ml of an ice-cooled toluene solution containing 18 μl (0.13 mmol) of diisopropylamine, and the mixture was stirred for 10 minutes. At the end of this time, 125 μl (0.12 mmol) of a hexane solution containing 0.97M of diethylaluminium chloride was added and the mixture was stirred for a further 20 minutes ac this temperature. The diethylaluminium diisopropylamide solution thus obtained was added to 2 ml of an ice-cooled tetrahydrofuran solution containing 43 mg (0.12 mol) of (2S,4S)-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-mercaptopyrrolidine, and stirred for 15 minutes at this temperature. At the end of this time, 1 ml of a tetrahydrofuran solution containing 68 mg (0.10 mmol) of 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 39) was added to the reaction mixture, and the mixture was stirred for 105 minutes. A saturated aqueous solution of ammonium chloride and then ethyl acetate were added, and the precipitate which formed was removed. The organic layer was separated, and washed with water and then with a saturated aqueous solution of sodium chloride. The solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 10 g of silica gel, using a 1:3 by volume mixture of benzene and ethyl acetate as the eluent, to obtain 60 mg of a fraction containing the title compound in a yield of 74%. This fraction showed a purity of 56% as determined by the area ratio according to liquid chromatography.

後処理

  1. additionwas added to the reaction mixture
  2. stirringthe mixture was stirred for 105 minutes
  3. customthe precipitate which formed
  4. customwas removed
  5. customThe organic layer was separated
  6. washwashed with water
  7. customThe solvent was then removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through 10 g of silica gel
  9. additionby volume mixture of benzene and ethyl acetate as the eluent
  10. customto obtain 60 mg of a fraction

出典と根拠

ORDレコード
ord-8831a9974bb74efe9f379dd4b07677a5
出典データセット
uspto-grants-1997_10
特許番号
US05681951

関連ノート

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