Sodium Iodide → Pivaloyloxymethyl (3S, 5R)-penam-3-carboxylate 1,1-Dioxide

HRID 1733204Notes

Reaction equation

HRID 1733204 reaction equation
[S:1]1(=[O:13])(=[O:12])[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[C@@H:3]([C:9]([OH:11])=[O:10])[CH2:2]1.C(N(C(C)C)CC)(C)C.[C:23]([O:29][CH2:30]Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[S:1]1(=[O:13])(=[O:12])[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[C@@H:3]([C:9]([O:11][CH2:30][O:29][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[O:10])[CH2:2]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 13518352(3S, 5R)-penam-3-carboxylic acid 1,1-dioxide

Product 1

HCID 86737398Pivaloyloxymethyl (3S, 5R)-penam-3-carboxylate 1,1-Dioxide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2.05 g of (3S, 5R)-penam-3-carboxylic acid 1,1-dioxide in 10 ml of N,N-dimethylformamide is added 1.30 g of diisopropylethylamine followed by 1.50 g of chloromethyl pivalate and 50 mg of sodium iodide at ca. 0° C. The reaction mixture is stirred at ca. 0° C. for 30 minutes and then at room temperature for 24 hours. The reaction mixture is then diluted with ethyl acetate and water and the pH of the aqueous phase is adjusted to 7.5. The ethyl acetate layer is separated and washed three times with water and once with saturated sodium chloride solution. The ethyl acetate solution is then dried using anhydrous sodium sulfate, and evaporated in vacuo to give the title compound.

Workup

  1. waitat room temperature for 24 hours
  2. customThe ethyl acetate layer is separated
  3. washwashed three times with water
  4. dry with materialThe ethyl acetate solution is then dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c16c55450f084c09aa36520f2e2942bf
Source dataset
uspto-grants-1980_12
Patent number
US04241050

Reaction notes

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