Sodium Iodide → HCID 69007968, compound

HRID 2403078Notes

Reaction equation

HRID 2403078 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([S:22][CH2:23][C:24]=2[CH2:25]Cl)[CH:20]([NH:27][C:28](=[O:30])[CH3:29])[C:19]3=[O:31])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:32].[Na+]>CC(C)=O>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([S:22][CH2:23][C:24]=2[CH2:25][I:32])[CH:20]([NH:27][C:28](=[O:30])[CH3:29])[C:19]3=[O:31])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 69009104HCID 69009104, compound

Product 1

HCID 69007968HCID 69007968, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-(acetylamino)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (1, 155 mg, 0.34 mmol) and sodium iodide (253 mg, 1.7 mmol) in 5 mL of acetone was stirred for 1 hr at room temperature. The reaction mixture was concentrated on the rotary evaporator and diluted with 5 mL water. The suspension was extracted with 25 mL of ethyl acetate, and the organic phase was washed with 10% sodium thiosulfate (5 mL×2), brine (5 mL×3) and dried over anhydrous magnesium sulfate. The slightly orange powder 2 (152 mg, 0.45 mmol) was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated on the rotary evaporator
  2. additiondiluted with 5 mL water
  3. extractionThe suspension was extracted with 25 mL of ethyl acetate
  4. washthe organic phase was washed with 10% sodium thiosulfate (5 mL×2), brine (5 mL×3)
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-112409f1fb7b413f9045332befdb4a2a
Source dataset
uspto-grants-2014_08
Patent number
US08802387B2

Reaction notes

Loading…