Sodium Iodide → HCID 54199176, compound

HRID 346219

Reaction equation

HRID 346219 reaction equation
[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

Participants

7

Reactant 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, compound

Product 1

HCID 54199176HCID 54199176, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d2dfe5760cff482cb53ac8a895c9852a
Source dataset
uspto-grants-1991_10
Patent number
US05061702

Linked notes

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