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 235771ノート

反応式

HRID 235771 の反応式
[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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9dae6f68a64454d8924bc873fd93bcd
出典データセット
uspto-grants-1987_02
特許番号
US04640915

反応ノート

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