Methyl Isobutyl Ketone → Sodium (Z)-(2S,3S,5R)-3-(2-cyanoethenyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263744

반응식

HRID 263744 반응식
[C:1](/[CH:3]=[CH:4]\[C@:5]1([CH3:31])[S:11](=[O:13])(=[O:12])[C@H:10]2[N:7]([C:8](=[O:14])[CH2:9]2)[C@H:6]1[C:15]([O:17]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16])#[N:2].CC(CC(C)C)=O.C(C(CCCC)C([O-])=O)C.[Na+:49]>C1C(O)=CC=CC=1C>[C:1](/[CH:3]=[CH:4]\[C@:5]1([CH3:31])[S:11](=[O:13])(=[O:12])[C@H:10]2[N:7]([C:8](=[O:14])[CH2:9]2)[C@H:6]1[C:15]([O-:17])=[O:16])#[N:2].[Na+:49]

참가 물질

5

반응물 3

HCID 7909Methyl Isobutyl KetoneHCID 10812820benzhydryl (Z)-(2S,3S,5R)-3-(2-cyanoethenyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylateHCID 23672331Sodium 2-ethylhexanoate

생성물 1

HCID 44347781Sodium (Z)-(2S,3S,5R)-3-(2-cyanoethenyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

시약·촉매·용매 1

HCID 342M-Cresol용매

반응 조건

온도
50 °C

실험 절차

95 mg (0.2 mmol) of benzhydryl (Z)-(2S,3S,5R)-3-(2-cyanoethenyl)- 3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 3 ml of m-cresol and stirred at 50° C. for 45 minutes. The reaction mixture was treated with 10 ml of isobutyl methyl ketone and 120 μl of sodium 2-ethylcaproate (2N in ethyl acetate, 1.1 eq.). The mixture was extracted twice with 3 ml of water each time, the combined aqueous phases are washed with 10 ml of isobutyl methyl ketone and lyophilized. The yellow lyophilizate was dissolved in 1.3 ml of water and chromatographed over polymeric hydrophobic gel. Yield: 50 mg (80%) of colorless lyophilizate IR (KBr): 2222, 1782, 1626, 1395, 1323, 1141 cm-1 1 H-NMR (250MHz, D2O): δ[ppm]=1.94(s,3H), 3.47(dd,1H,J=16Hz, 1.6Hz, 6-H), 3.73(dd, 1H, J=16Hz, 4.4Hz, 6-H), 4.80(s,1H,2-H), 5.19(dd, 1H, J=16Hz, 4.4Hz,5-H), 6.15(d.1H,J=12Hz,=CH), 6.68 (d,1 H,J=12Hz,=CH).

후처리

  1. extractionThe mixture was extracted twice with 3 ml of water each time
  2. washthe combined aqueous phases are washed with 10 ml of isobutyl methyl ketone
  3. dissolutionThe yellow lyophilizate was dissolved in 1.3 ml of water
  4. customchromatographed over polymeric hydrophobic gel

출처 및 근거

ORD 기록
ord-56a208715fcd48fbb7c72d5f3d89da62
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05644053

연결된 노트

불러오는 중…