Sodium Iodide → HCID 131713180, compound

HRID 905449Notes

Reaction equation

HRID 905449 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:25])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.Br[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:29](=[O:30])[O:28]1.[I-].[Na+].C(OC(C)C)(C)C>CN(C)C=O.O.C(N(CC)CC)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:25])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O:22][CH:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:29](=[O:30])[O:28]4)=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7914Diisopropyl EtherHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 13171318179350-14-4

Product 1

HCID 131713180HCID 131713180, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 7-[(2-aminothiazol-4-yl)glyoxylamido]-3-vinyl-3-cephem-4-carboxylic acid (1.0 g) in N,N-dimethylformamide (10 ml) were added triethylamine (0.27 g), 3-bromophthalide (0.56 g) and sodium iodide (0.39 g) at 10° C. with stirring, and the stirring was continued at the same temperature for half an hour. After the reaction mixture was poured into water (50 ml), it was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1 by volume). The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate, followed by evaporation to give an oil, which was pulverized with diisopropyl ether to obtain phthalid-3-yl 7-[(2-aminothiazol-4-yl)glyoxylamido]-3-vinyl-3-cephem-4-carboxylate (1.0 g).

Workup

  1. waitthe stirring was continued at the same temperature for half an hour
  2. extractionwas extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1 by volume)
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customfollowed by evaporation
  6. customto give an oil, which

Sources & evidence

ORD record
ord-f30258778e6f4eb1954ec4a1b531681e
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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