Sodium Iodide → HCID 86608983, compound

HRID 495014Notes

Reaction equation

HRID 495014 reaction equation
[C:1]([CH2:4][N:5]1[C@H:8]([C@H:9]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[S:12])[CH3:10])[C@@H:7]([C@H:19]([OH:21])[CH3:20])[C:6]1=[O:22])([OH:3])=[O:2].[C:23]([O:29][CH2:30]Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].[I-].[Na+].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:13]1([C:11]([C@@H:9]([C@H:8]2[N:5]([CH2:4][C:1]([O:3][CH2:30][O:29][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[O:2])[C:6](=[O:22])[C@@H:7]2[C@H:19]([OH:21])[CH3:20])[CH3:10])=[S:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 56979190HCID 56979190, compound

Product 1

HCID 86608983HCID 86608983, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature (25° C.), 1.35 g (4.0 mmol) of (3S,4S)-1-carboxymethyl-4-[(1R)-1-(phenylthiocarbonyl)ethyl]-3-[(1R)-1-hydroxyethyl]-2-azetidinone was dissolved in 8 ml of dimethylformamide, and 1.20 (8.0 mmol) of-pivaloyloxymethyl chloride and 1.20 g (8.0 mmol) of sodium iodide were sequentially added thereto. Subsequently, 0.68 g (5.3 mmol) of diisopropylethylamine was added dropwise thereto, and stirring was performed at the same temperature for 6 hours. The reaction solution was diluted with 40 ml of ethyl acetate, and washing was performed several times using 5% aqueous sodium bicarbonate and water. The resulting ethyl acetate solution was dried over sodium sulfate, and then the solvent was removed by distillation. Thereby, 1.88 g of the target compound was produced.

Workup

  1. washwashing
  2. dry with materialThe resulting ethyl acetate solution was dried over sodium sulfate
  3. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-0857b51058d447e0bbe8ea23cc7a8ed6
Source dataset
uspto-grants-2009_05
Patent number
US07538212B2

Reaction notes

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