Potassium Phosphate, Dibasic → potassium (5R, 6R)-6-(1-hydroxy-1-methylethyl)-3-(tetrazolo[1,5-b]pyridazin-6-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 235776

反応式

HRID 235776 の反応式
[CH3:1][C:2]([C@@H:18]1[C:24](=[O:25])[N:23]2[C@@H:19]1[CH2:20][C:21]([S:39][C:40]1[CH:41]=[CH:42][C:43]3[N:44]([N:46]=[N:47][N:48]=3)[N:45]=1)=[C:22]2[C:26]([O:28]CC1C=CC([N+]([O-])=O)=CC=1)=[O:27])([O:4]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH3:3].P([O-])([O-])(O)=O.[K+:54].[K+]>O1CCCC1.C(O)C.[H][H].O.[Pt](=O)=O>[OH:4][C:2]([C@@H:18]1[C:24](=[O:25])[N:23]2[C@@H:19]1[CH2:20][C:21]([S:39][C:40]1[CH:41]=[CH:42][C:43]3[N:44]([N:46]=[N:47][N:48]=3)[N:45]=1)=[C:22]2[C:26]([O-:28])=[O:27])([CH3:3])[CH3:1].[K+:54]

参加物

7

反応物 2

HCID 24450Potassium Phosphate, DibasicHCID 56609997HCID 56609997、化合物

生成物 1

HCID 131715053potassium (5R, 6R)-6-(1-hydroxy-1-methylethyl)-3-(tetrazolo[1,5-b]pyridazin-6-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

試薬・触媒・溶媒 4

HCID 11139377Platinum dioxide monohydrate触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 178418361HCID 178418361、化合物溶媒

実験手順

A mixture of 4-nitrobenzyl (5R, 6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-3-(tetrazolo[1,5-b]pyridazin-6-ylthio)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate (0.4357 g), platinum (IV) oxide monohydrate (0.2179 g) in 0.047M aqueous dipotassium hydrogen phosphate (41.1 ml), tetrahydrofuran (52.3 ml) and ethanol (4.40 ml) was stirred for 3.7 hours in hydrogen gas under atmospheric pressure at ambient temperature. After the catalyst was filtered off, the filtrate was concentrated to half of the original volume. The aqueous concentrate was washed with diethyl ether (x3) and evaporated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion CHP-20P" (Trademark, manufactured by Mitsubishi Chemical Industries) (220 ml) eluting with water (1.50 l), 5% aqueous isopropyl alcohol (400 ml) and 10% aqueous isopropyl alcohol (400 ml). The fractions, whose IV spectra showed λ max 233.0 nm and 282.5 nm, were combined and lyophilized to give crude product (0.1459 g), which was chromatographed again on "Diaion CHP-20P" (130 ml) eluting with water (340 ml), 5% aqueous isopropyl alcohol (360 ml) and 10 aqueous isopropyl alcohol (200 ml). The fractions containing the desired compound were collected and lyophilized to give potassium (5R, 6R)-6-(1-hydroxy-1-methylethyl)-3-(tetrazolo[1,5-b]pyridazin-6-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.1299 g) as a yellow powder.

後処理

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated to half of the original volume
  3. concentrationThe aqueous concentrate
  4. washwas washed with diethyl ether (x3)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on nonionic adsorption resin "Diaion CHP-20P" (Trademark, manufactured by Mitsubishi Chemical Industries) (220 ml)
  7. washeluting with water (1.50 l), 5% aqueous isopropyl alcohol (400 ml) and 10% aqueous isopropyl alcohol (400 ml)
  8. customto give crude product (0.1459 g), which
  9. customwas chromatographed again on "Diaion CHP-20P" (130 ml)
  10. washeluting with water (340 ml), 5% aqueous isopropyl alcohol (360 ml) and 10 aqueous isopropyl alcohol (200 ml)
  11. additionThe fractions containing the desired compound
  12. customwere collected

出典と根拠

ORDレコード
ord-39501c0783b940c783f54cd5474172f0
出典データセット
uspto-grants-1987_02
特許番号
US04640915

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