Sodium Iodide → HCID 86602586, compound

HRID 2113181Notes

Reaction equation

HRID 2113181 reaction equation
CN(C)C=O.[C:6]([CH2:9][N:10]1[C@H:13]([C@H:14]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[S:17])[CH3:15])[C@@H:12]([C@H:25]([OH:27])[CH3:26])[C:11]1=[O:28])([OH:8])=[O:7].[C:29]([O:35][CH2:36]Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].[I-].[Na+].C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]([C@@H:14]([C@H:13]2[N:10]([CH2:9][C:6]([O:8][CH2:36][O:35][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:7])[C:11](=[O:28])[C@@H:12]2[C@H:25]([OH:27])[CH3:26])[CH3:15])=[S:17])=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 18636525(3S,4S)-1-carboxymethyl-4-[(1R)-1-(p-chlorophenylthiocarbonyl)ethyl]-3-[(1R)-1-hydroxyethyl]-2-azetidinone

Product 1

HCID 86602586HCID 86602586, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In18 ml of dimethylformamide, was dissolved 8.18 g (22.0 mmol) of (3S,4S)-1-carboxymethyl-4-[(1R)-1-(p-chlorophenylthiocarbonyl)ethyl]-3-[(1R)-1-hydroxyethyl]-2-azetidinone at room temperature. To the resulting solution, were successively added 5.5 ml (40.0 mmol) of pivaloyloxymethyl chloride and 5.75 g (40.3 mmol) of sodium iodide, and was added dropwise 4.2 ml (25.3 mmol) of diisopropylethylamine, followed by stirring the mixture for 20 hours at the same temperature. The reaction mixture was diluted with 120 ml of toluene. The toluene solution was washed with 2.5% aqueous sodium bicarbonate solution and water, each several times. The resulting toluene solution was dried over sodium sulfate, and then the solvent was removed by evaporation. The resulting oily residue was dissolved in 60 ml of toluene at room temperature. To the resulting solution was added 120 ml of hexane, precipitating a crystal, which was filtered and washed to obtain 9.46 g of a white crystal of the title compound (yield: 92.7%).

Workup

  1. washThe toluene solution was washed with 2.5% aqueous sodium bicarbonate solution and water
  2. dry with materialThe resulting toluene solution was dried over sodium sulfate
  3. customthe solvent was removed by evaporation
  4. dissolutionThe resulting oily residue was dissolved in 60 ml of toluene at room temperature
  5. additionTo the resulting solution was added 120 ml of hexane
  6. customprecipitating a crystal, which
  7. filtrationwas filtered
  8. washwashed

Sources & evidence

ORD record
ord-252ae7c313e6402c84d9e232715809db
Source dataset
uspto-grants-2009_04
Patent number
US07524952B2

Reaction notes

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