Epichlorohydrin → HCID 22313555, compound

HRID 584607Notes

Reaction equation

HRID 584607 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]([CH3:13])([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[O:5].C([O-])([O-])=O.[K+].[K+].Cl[CH2:25][CH:26]1[CH2:28][O:27]1>C(#N)C.CCOC(C)=O>[CH3:13][C:7]([NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[O:1][CH2:25][CH:26]1[CH2:28][O:27]1)([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 22313664HCID 22313664, compound

Product 1

HCID 22313555HCID 22313555, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-[(2-hydroxybenzoyl)amino]-2-methylpropanoate, K2CO3 (20 mmol, 2.68 g) and 2-(chloromethyl)oxirane (22 mmol, 2.03 g) in acetonitrile (60 ml) was stirred at reflux temperature overnight. The reaction mixture was diluted with EtOAc and washed with 1.8% HCl/aq (250 ml) and sat. NaCl/aq (250 ml). The organic phase was dried over Na2SO4 and concentrated at reduced pressure. The residue was purified on C18-column (H2O:CH3CN, 0.1M NH4OAc buffer, gradient 10% to 95% CH3CN) to give the subtitle compound (244 mg, 5% yield, two steps).

Workup

  1. temperatureat reflux temperature overnight
  2. washwashed with 1.8% HCl/aq (250 ml) and sat. NaCl/aq (250 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified on C18-column (H2O:CH3CN, 0.1M NH4OAc buffer, gradient 10% to 95% CH3CN)

Sources & evidence

ORD record
ord-89a0650f4c314785a44134c85ad54c59
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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