Triphenylphosphine → HCID 68840887, compound

HRID 1889272Notes

Reaction equation

HRID 1889272 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][OH:23])=[O:9])([CH3:6])[CH3:5].[F:25][C:26]1[CH:27]=[C:28](O)[CH:29]=[C:30]([F:32])[CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][O:23][C:28]1[CH:27]=[C:26]([F:25])[CH:31]=[C:30]([F:32])[CH:29]=1)=[O:9])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 759283,5-DifluorophenolHCID 5363146Diisopropyl azodicarboxylateHCID 68842699HCID 68842699, compound

Product 1

HCID 68840887HCID 68840887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 67 mg 2-{[1-(2-hydroxy-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester and 29 mg 3,5-difluorophenol in 1 ml THF at 0° C. 58 mg triphenyl phosphine and 46 μl diisopropylazodicarboxylate were added. After 16 h at room temperature the reaction was concentrated in vacuo and after chromatography on silica (ethyl acetate/heptane) 80 mg 2-({1-[2-(3,5-difluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester were obtained.

Workup

  1. customat 0° C
  2. concentrationAfter 16 h at room temperature the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-fd7fb4e629dc44fbb153746d1b9c6462
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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