Sodium Iodide → HCID 88496309, compound

HRID 893754Notes

Reaction equation

HRID 893754 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:46]/[O:47][C:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])([CH3:50])[CH3:49])/[C:27]([NH:29][CH:30]2[C:44](=[O:45])[N:32]3[C:33]([C:41]([O-:43])=[O:42])=[C:34](/[CH:37]=[CH:38]\[CH2:39]Cl)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:58].[Na+]>CC(C)=O.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:46]/[O:47][C:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])([CH3:50])[CH3:49])/[C:27]([NH:29][CH:30]2[C:44](=[O:45])[N:32]3[C:33]([C:41]([O:43][CH:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[O:42])=[C:34](/[CH:37]=[CH:38]/[CH2:39][I:58])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 5238Sodium IodideHCID 178451068HCID 178451068, compound

Product 1

HCID 88496309HCID 88496309, compoundYield 204.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-[(Z)-3-chloro-1-propen-1-yl]-3-cephem-4-carboxylate (IXa) (1.23 g, 1.24 mmole) in acetone (5 ml) was added a solution of sodium iodide (560 mg, 3.72 mmol) in acetone (7 ml). The mixture was stirred at room temperature for 1.5 hour, and diluted with ethyl acetate (150 ml) and aqueous sodium thiosulfate solution. The organic layer was separated, dried over magnesium sulfate, and concentrated to give 1.38 g of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-[(E)-3-iodo-1-propen-1-yl]-3-cephem-4-carboxylate (Xa) (see also Example 23 below) as an amorphous powder. Compound Xa was dissolved in ether (50 ml). The insoluble was filtered off and the filtrate was chilled in an ice-water bath, and was treated with a solution of 5,6-diacetoxy-2-methyl-2-isoindoline (600 mg, 2.4 mmol) in ether (50 ml). The mixture was stirred over 30 min, and the precipitate was collected by filtration to obtain 446 mg (27% yield) of the title iodide as a tan powder.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e8abb457dbb64227be4cb96527876848
Source dataset
uspto-grants-1992_06
Patent number
US05126336

Reaction notes

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