Sodium Iodide → HCID 88496309, compound

HRID 893757Notes

Reaction equation

HRID 893757 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]\[C:5]1[CH2:6][S:7][C@@H:8]2[CH:28]([NH:29][C:30](=[O:69])/[C:31](=[N:57]\[O:58][C:59]([CH3:68])([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH3:60])/[C:32]3[N:33]=[C:34]([NH:37][C:38]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[S:35][CH:36]=3)[C:27](=[O:70])[N:9]2[C:10]=1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[I-:71].[Na+]>CC(C)=O.C(OCC)(=O)C>[I:71][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH2:6][S:7][C@@H:8]2[CH:28]([NH:29][C:30](=[O:69])/[C:31](=[N:57]\[O:58][C:59]([CH3:68])([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH3:60])/[C:32]3[N:33]=[C:34]([NH:37][C:38]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[S:35][CH:36]=3)[C:27](=[O:70])[N:9]2[C:10]=1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 88496688HCID 88496688, compound

Product 1

HCID 88496309HCID 88496309, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of diphenylmethyl 3-[(Z)-3-chloro-1-propen-1-yl]-7-[(Z)-2-(1-methyl-1-t-butoxycarbonylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxy-late (IXa) (488 mg, 0.5 mmol) and sodium iodide (225 mg, 1.5 mmol) in acetone (5 ml) was stirred at room temperature for 2 hours and diluted with ethyl acetate. The organic layer was washed with an aqueous sodium thiosulfate, dried over anhydrous MgSO4 and concentrated to afford 546 mg (yield, quantitative) of the title product.

Workup

  1. washThe organic layer was washed with an aqueous sodium thiosulfate
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f2728693ac434cf78fd68fccf4038027
Source dataset
uspto-grants-1992_06
Patent number
US05126336

Reaction notes

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