Ethanol → HCID 86741290, 화합물

HRID 235765

반응식

HRID 235765 반응식
[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[S:41][C:42]([CH3:45])=[N:43][N:44]=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].C(O)C.P([O-])([O-])(O)=O.[K+:54].[K+].O>O1CCOCC1.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[S:41][C:42]([CH3:45])=[N:43][N:44]=1)=[C:22]2[C:26]([O-:28])=[O:27])([CH3:3])[CH3:1].[K+:54]

참가 물질

7

반응물 4

HCID 702EthanolHCID 962WaterHCID 24450Potassium Phosphate, DibasicHCID 54564139HCID 54564139, 화합물

생성물 1

HCID 86741290HCID 86741290, 화합물

시약·촉매·용매 2

HCID 11139377Platinum dioxide monohydrate촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 4-nitrobenzyl (5R,6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50 mg) and platinum (IV) oxide monohydrate (50 mg) in a mixture of dioxane (6 ml), ethanol (0.5 ml), 0.1M aqueous dipotassium hydrogen phosphate (2.28 ml) and water (2.5 ml) was shaken for 1.5 hours under a hydrogen atmosphere (40 psi) at ambient temperature. The catalyst was filtered off and the filtrate was concentrated to half of the original volume. The aqueous concentrate was washed three times with diethyl ether and evaporated in vacuo. The residue was dissolved in water (25 ml) and potassium chloride (1.25 g) was added. The aqueous solution was chromatographed on non-ionic adsorption resin, "Diaion HP-20 AG" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (1.2×22 cm), eluting with water (150 ml) and aqueous isopropyl alcohol (5 to 30%, 100 ml). The fractions, whose UV spectra showed λmax 293 nm, were combined and lyophilized to give potassium (5R,6R)-6-(1-hydroxy-1-methylethyl)-3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (16.9 mg).

후처리

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to half of the original volume
  3. concentrationThe aqueous concentrate
  4. washwas washed three times with diethyl ether
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in water (25 ml)
  7. additionpotassium chloride (1.25 g) was added
  8. customThe aqueous solution was chromatographed on non-ionic adsorption resin, "Diaion HP-20 AG" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (1.2×22 cm)
  9. washeluting with water (150 ml) and aqueous isopropyl alcohol (5 to 30%, 100 ml)

출처 및 근거

ORD 기록
ord-3d56997817514848b63032c24278a152
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04640915

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