benzhydryl (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate → Sodium (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263746

反応式

HRID 263746 の反応式
[Cl:1]/[CH:2]=[CH:3]/[C@:4]1([CH3:30])[S:10](=[O:12])(=[O:11])[C@H:9]2[N:6]([C:7](=[O:13])[CH2:8]2)[C@H:5]1[C:14]([O:16]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15].C(C(CCCC)C([O-])=O)C.[Na+:41]>C1C(O)=CC=CC=1C.CC(CC(C)C)=O>[Cl:1]/[CH:2]=[CH:3]/[C@:4]1([CH3:30])[S:10](=[O:12])(=[O:11])[C@H:9]2[N:6]([C:7](=[O:13])[CH2:8]2)[C@H:5]1[C:14]([O-:16])=[O:15].[Na+:41]

参加物

5

反応物 2

HCID 10742000benzhydryl (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylateHCID 23672331Sodium 2-ethylhexanoate

生成物 1

HCID 86750938Sodium (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

試薬・触媒・溶媒 2

HCID 342M-Cresol溶媒HCID 7909Methyl Isobutyl Ketone溶媒

反応条件

温度
50 °C

実験手順

385 mg (0.86 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(2-chloro- vinyl) -3- methyl-4,4,7-trioxo-4-thia- 1-aza-bicyclo [3.2.0]heptane-2-carboxylate are dissolved in 2.3 ml of m-cresol under argon and stirred at 50° C. for 4 hours. Subsequently, the mixture was diluted with 15 ml of isobutyl methyl ketone, treated with 0.50 ml of sodium 2-ethylcaproate (2N solution in ethyl acetate) and extracted three times with 8 ml of water each time. The combined aqueous phases were washed once with 10 ml of isobutyl methyl ketone, lyophilized and the lyophilizate obtained was chromatographed over polymeric hydrophobic gel with water as the eluent. Yield: 57 mg (32%) MS: (M--Na)- 278.2 IR (KBr): 1780, 1626, 1564, 1417, 1329, 1145 cm-1

後処理

  1. extractionextracted three times with 8 ml of water each time
  2. washThe combined aqueous phases were washed once with 10 ml of isobutyl methyl ketone
  3. customthe lyophilizate obtained
  4. customwas chromatographed over polymeric hydrophobic gel with water as the eluent

出典と根拠

ORDレコード
ord-5e606b15b4c5498c94046bd224fef880
出典データセット
uspto-grants-1997_07
特許番号
US05644053

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