Triphenylphosphine → Ethyl 3-methoxy-4-[2-methyl-2-(benzyloxycarbonyl)aminoethoxy]benzoate

HRID 354471Notes

Reaction equation

HRID 354471 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].C[N:16]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:17][CH2:18]O.[CH:30]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:14][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[O:1][CH2:30][CH:17]([CH3:18])[NH:16][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12038Ethyl vanillateHCID 5363146Diisopropyl azodicarboxylateHCID 13279869N-Cbz-N-methyl-2-aminoethanol

Product 1

HCID 23512341Ethyl 3-methoxy-4-[2-methyl-2-(benzyloxycarbonyl)aminoethoxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-hydroxy-3-methoxybenzoate (2.01 g, 10.25 mmol), N-methyl-N-(benzyloxycarbonyl)ethanolamine (2.11 g, 10.08 mmol), PPh3 (3.26 g, 12.43 mmol) in THF was added DIAD (2.65 mL, 13.46 mmol) and the reaction mixture was heated under reflux overnight. The mixture was evaporated, and the residue was subjected to short column chromatography on silica-gel with n-hexane/EtOAc (5:1, v/v) as eluent to give ethyl 3-methoxy-4-[2-methyl-2-(benzyloxycarbonyl)aminoethoxy]benzoate as a crude product.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customThe mixture was evaporated

Sources & evidence

ORD record
ord-a8da173358d44d44806fded2c07675f9
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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