Sodium Iodide → Phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 1088134Notes

Reaction equation

HRID 1088134 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][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.C(N(CC)CC)C.Br[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:35](=[O:36])[O:34]1.[I-].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O:22][CH:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:35](=[O:36])[O:34]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 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 88469260Unii-nyh6qmq9H0

Product 1

HCID 88469456Phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylateYield 55.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (2.0 g) in N,N-dimethylformamide (15 ml) were added triethylamine (0.55 g), 3-bromophthalide (1.2 g) and sodium iodide (0.82 g) in turn in a stream of nitrogen, and the mixture was stirred at ambient temperature for half an hour. After the reaction mixture was poured into a mixture of ethyl acetate (300 ml) and water (200 ml), the organic layer was separated out, washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate, followed by treating with charcoal. After the filtrate was concentrated and thereto was added diethyl ether. The precipitated substance was collected by filtration to obtain phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (1.5 g).

Workup

  1. customthe organic layer was separated out
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  4. additionby treating with charcoal
  5. concentrationAfter the filtrate was concentrated
  6. additionwas added diethyl ether
  7. filtrationThe precipitated substance was collected by filtration

Sources & evidence

ORD record
ord-d09274dd3a8345929e5450c243de98d3
Source dataset
uspto-grants-1990_10
Patent number
US04960889

Reaction notes

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