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

HRID 346219

反応式

HRID 346219 の反応式
[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

参加物

7

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2dfe5760cff482cb53ac8a895c9852a
出典データセット
uspto-grants-1991_10
特許番号
US05061702

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