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

반응식

HRID 263746 반응식
[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]

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 2

HCID 342M-Cresol용매HCID 7909Methyl Isobutyl Ketone용매

반응 조건

온도
50 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-5e606b15b4c5498c94046bd224fef880
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05644053

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