Ethanol → potassium (5R, 6S)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 235771노트

반응식

HRID 235771 반응식
[CH3:1][O:2][C:3]([C@H:6]1[C:12](=[O:13])[N:11]2[C@@H:7]1[CH2:8][C:9]([S:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)=[C:10]2[C:14]([O:16]CC1C=CC([N+]([O-])=O)=CC=1)=[O:15])([CH3:5])[CH3:4].P([O-])([O-])(O)=O.[K+:39].[K+].O.C(O)C>O1CCOCC1.[Pt](=O)=O>[CH3:1][O:2][C:3]([C@H:6]1[C:12](=[O:13])[N:11]2[C@@H:7]1[CH2:8][C:9]([S:27][C:28]1[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=1)=[C:10]2[C:14]([O-:16])=[O:15])([CH3:5])[CH3:4].[K+:39]

참가 물질

7

반응물 4

HCID 702EthanolHCID 962WaterHCID 24450Potassium Phosphate, DibasicHCID 572670844-nitrobenzyl (5R, 6S)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

생성물 1

HCID 86741294potassium (5R, 6S)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 4-nitrobenzyl (5R, 6S)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (371.0 mg) and platinum (IV) oxide (123.7 mg) in a mixture of dioxane (44.5 ml), 0.1M aqueous dipotassium hydrogen phosphate (23.7 ml), water (5.98 ml) and ethanol (3.71 ml) was shaken for an hour under a hydrogen atmosphere (50 psi) at ambient temperature. The reaction mixture was filtered using super cell. The filter cake was washed with water, and the combined filtrates were concentrated. The residual aqueous layer was washed three times with diethyl ether at 0° C. and concentrated. After addition of potassium chloride (9 g), the resultant aqueous solution (180 ml) was chromatographed on non-ionic adsorption resin "Diaion HP-20 AG" (24×300 mm) eluting successively with water (420 ml), 5% aqueous isopropyl alcohol (420 ml) and 10% aqueous isopropyl alcohol (420 ml). The fractions, whose UV spectrum showed λ max 303 nm, were collected, concentrated and lyophilized to give potassium (5R, 6S)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (208.7 mg) as a white powder.

후처리

  1. filtrationThe reaction mixture was filtered
  2. washThe filter cake was washed with water
  3. concentrationthe combined filtrates were concentrated
  4. washThe residual aqueous layer was washed three times with diethyl ether at 0° C.
  5. concentrationconcentrated
  6. additionAfter addition of potassium chloride (9 g)
  7. customthe resultant aqueous solution (180 ml) was chromatographed on non-ionic adsorption resin "Diaion HP-20 AG" (24×300 mm)
  8. washeluting successively with water (420 ml), 5% aqueous isopropyl alcohol (420 ml) and 10% aqueous isopropyl alcohol (420 ml)
  9. customwere collected
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c9dae6f68a64454d8924bc873fd93bcd
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04640915

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