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

HRID 350535Notes

Reaction equation

HRID 350535 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-hydoxy-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-ecd940ddecda448d93e0bcbc9ea2310b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…