Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI) → HCID 68662149, compound

HRID 1864011Notes

Reaction equation

HRID 1864011 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[CH2:13]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:14]1[O:16][CH2:15]1>CO>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][CH2:15][C@H:14]([OH:16])[CH2:13][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)HCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 68662149HCID 68662149, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2,4-dimethoxybenzylamine (1.00 g, 5.99 mmol) in MeOH (30 mL) at room temperature was added benzyl(S)-(+)-glycidyl ether (0.88 g, 5.40 mmol). After 12 h the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (75 mL) and washed sequentially with 1 N HCl (25 mL) and brine (25 mL). The solution was dried over MgSO4, filtered and the solvent removed under reduced pressure to give 1.35 g of the crude oil that was used in the next step without further purification. MS (ES+) m/z 332.2 (M+H)+.

Workup

  1. concentrationAfter 12 h the reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (75 mL)
  3. washwashed sequentially with 1 N HCl (25 mL) and brine (25 mL)
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e53740772ff84317833ecf77ca1b8169
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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