Ethoxalyl chloride → HCID 21498802, compound

HRID 928362Notes

Reaction equation

HRID 928362 reaction equation
[OH:1][NH:2][C:3](=[NH:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:12]([O:14][C:15](=[O:19])[C:16](Cl)=O)[CH3:13].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH2:12]([O:14][C:15]([C:16]1[O:1][N:2]=[C:3]([CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:11]=1)=[O:19])[CH3:13]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 516892Sodium BicarbonateHCID 178510798HCID 178510798, compound

Product 1

HCID 21498802HCID 21498802, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of N-Hydroxy-2-phenyl-acetamidine (1 g, 6.7 mmol) in 7 mL ethyl acetate was added a solution of Chloro-oxo-acetic acid ethyl ester (1.5 g, 10.7 mmol) in 7 mL ethyl acetate at 0° C. The mixture was stirred for 1.5 h at room temperature and then heated to 80° C. for 2.5 h. The reaction mixture was treated with aq. NaHCO3-solution and extracted with ethyl acetate. The organic layers were dried over MgSO4 and evaporated in vacuo. The crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40ml/min) to yield the title compound. LCMS (method A) RtA=1.938 min; [M+H]+=233.1.

Workup

  1. temperatureheated to 80° C. for 2.5 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40ml/min)

Sources & evidence

ORD record
ord-582374f986224377948f7c2c16febbbe
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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