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

HRID 1088131Notes

Reaction equation

HRID 1088131 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]([O-:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:26]([O:33][CH2:34]I)(=[O:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[I-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[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][CH2:34][O:33][C:26](=[O:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 12775069Iodomethyl hexanoateHCID 88469259HCID 88469259, compound

Product 1

HCID 88469331Hexanoyloxymethyl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylateYield 58.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylate (2.0 g) in N,N-dimethylformamide (20 ml) were added iodomethyl hexanoate (3.4 g) and sodium iodide (3.1 g) in a stream of nitrogen, and the mixture was stirred at ambient temperature for 1.5 hours. After the reaction mixture was poured into a mixture of ethyl acetate (200 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. The filtrate was concentrated, and thereto was added diisopropyl ether, followed by collecting the precipitated substance by filtration to obtain hexanoyloxymethyl 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. concentrationThe filtrate was concentrated
  6. additionwas added diisopropyl ether
  7. customby collecting the precipitated substance
  8. filtrationby filtration

Sources & evidence

ORD record
ord-67e6d19ab72e4ac8843741593782ff02
Source dataset
uspto-grants-1990_10
Patent number
US04960889

Reaction notes

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