Sodium Iodide → (6R,7R)-7-phenylacetamido-3-[2-(3,4-diacetoxyphenyl)vinyl]ceph-3-em-4-carboxylic acid p-methoxybenzyl ester

HRID 346219

반응식

HRID 346219 반응식
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30]Cl)=[O:10])=[CH:5][CH:4]=1.[I-].[Na+].[C:36]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:55]([O:58][C:59]1[C:66]([O:67][C:68](=[O:70])[CH3:69])=[CH:65][CH:64]=[CH:63][C:60]=1C=O)(=[O:57])[CH3:56].C(=O)(O)[O-].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH:30]=[CH:36][C:63]2[CH:64]=[CH:65][C:66]([O:67][C:68](=[O:70])[CH3:69])=[C:59]([O:58][C:55](=[O:57])[CH3:56])[CH:60]=2)=[O:10])=[CH:5][CH:4]=1

참가 물질

7

반응물 5

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 19990370HCID 19990370, 화합물

생성물 1

HCID 54199176(6R,7R)-7-phenylacetamido-3-[2-(3,4-diacetoxyphenyl)vinyl]ceph-3-em-4-carboxylic acid p-methoxybenzyl ester수율 45.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution (20 ml) in acetone of 2.6004 g of (6R, 7R)-7-phenylacetamido-3-chloromethylceph-3-em-4-carboxylic acid p-methoxybenzyl ester were dissolved 0.787 g of sodium iodide and 1.377 g of triphenylphosphine and the mixture was stirred for 1 hour. The reaction mixture was concentrated under a reduced pressure, and 25 ml of methylene chloride and 25 ml of water were added to the residue to form two layers. To the reaction mixture, 5.555 g of 2,3-diacetoxybenzaldehyde and 1.47 g of sodium bicarbonate were added and the mixture was stirred for 14 hours at room temperature. The resulting dichloromethane layer was separated, concentrated under a reduced pressure, and was then purified by flash column chromatography using Wako Gel C-300 (300 g, Wako Junyaku KK) (eluent, benzene:ethyl acetate=5:1). The product, (6R,7R)-7-phenylacetamido-3-[2-(3,4-diacetoxyphenyl)vinyl]ceph-3-em-4-carboxylic acid p-methoxybenzyl ester (1.570 g, cis isomer) was obtained.

후처리

  1. concentrationThe reaction mixture was concentrated under a reduced pressure, and 25 ml of methylene chloride and 25 ml of water
  2. additionwere added to the residue
  3. customto form two layers
  4. stirringthe mixture was stirred for 14 hours at room temperature
  5. customThe resulting dichloromethane layer was separated
  6. concentrationconcentrated under a reduced pressure
  7. customwas then purified by flash column chromatography

출처 및 근거

ORD 기록
ord-d2dfe5760cff482cb53ac8a895c9852a
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05061702

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