Dimethylphosphite → HCID 57925972, compound

HRID 1013485Notes

Reaction equation

HRID 1013485 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[N:11]/[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[P:20]([O-:25])([O:23][CH3:24])[O:21][CH3:22]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[P:20]([O:23][CH3:24])([O:21][CH3:22])=[O:25])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 21884954DimethylphosphiteHCID 178497920HCID 178497920, compound

Product 1

HCID 57925972HCID 57925972, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[(E)-Benzylimino-methyl]-benzoic acid methyl ester (0.50 g, 1.97 mmol) was made 0.3 M in dimethyl phosphite (6.5 mL) and to this stirring solution was added catalytic N,N,N,′,N′-tetramethyl-guanidine (0.02 g, 0.20 mmol). After stirring at ambient temperature for 4 hours the reaction mixture was diluted with EtOAc and washed with 1M aqueous NaOH (3×). The organic layer was washed further with brine, then dried (MgSO4) and concentrated in vacuo. MPLC purification (10-70% EtOAc in CH2Cl2) gave the title compound: MS: cal'd 364 (MH+), exp 364 (MH+)

Workup

  1. washwashed with 1M aqueous NaOH (3×)
  2. washThe organic layer was washed further with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customMPLC purification (10-70% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-a12f57886f0143fd865e671961e29b91
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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