Sodium Iodide → HCID 131722365, compound

HRID 568256Notes

Reaction equation

HRID 568256 reaction equation
[I-:1].[Na+].[Br-].[C:4]([NH2:8])(=[O:7])[CH2:5][CH3:6].C(OC([N:15]1[C@H:19](/[CH:20]=[CH:21]/[C:22]2[N:23]3[CH:29]=[N:28][CH:27]=[C:24]3[S:25][CH:26]=2)[CH2:18][C@H:17]([S:30][C:31]2[C@H:32]([CH3:48])[C@@H:33]3[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:34]3[C:35]=2[C:36](OCC=C)=[O:37])[CH2:16]1)=O)C=C>CC(C)=O.CN(C=O)C>[C:4]([CH2:5][CH2:6][N:28]1[CH:27]=[C:24]2[S:25][CH:26]=[C:22](/[CH:21]=[CH:20]/[C@H:19]3[NH:15][CH2:16][C@@H:17]([S:30][C:31]4[C@H:32]([CH3:48])[C@@H:33]5[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:34]5[C:35]=4[C:36]([I:1])=[O:37])[CH2:18]3)[N:23]2[CH2:29]1)(=[O:7])[NH2:8]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 21262415HCID 21262415, compoundHCID 131722366HCID 131722366, compound

Product 1

HCID 131722365HCID 131722365, compoundYield 3.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium iodide (70 mg) and 71 mg of propionamide bromide are added to a solution of 55 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[2(E)-(imidazo[5,1-b]thiazol-3-yl)ethenyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, described in Example 38-a) in 1 ml of acetone and 0.5 ml of DMF, and the mixture is stirred in a light-shielded state at room temperature for 36 hr. The solvent is removed under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1). The procedure of Example 49-a) is repeated, except that the purification product prepared just above is used. Thus, 2 mg of the title compound is prepared.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by column chromatography on Sephadex
  3. customprepared just above

Sources & evidence

ORD record
ord-2c7829600af14f40960842427193314d
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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