Triphenylphosphine → 3-Benzyloxy-7-[2-(3-benzyloxy-2-dimethylcarbamoylphenoxy)-ethoxy]-naphthalene-2-carboxylic acid methyl ester

HRID 643881Notes

Reaction equation

HRID 643881 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][CH2:25][OH:26])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].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.[CH2:60]([O:67][C:68]1[CH:78]=[CH:77][CH:76]=[C:75](O)[C:69]=1[C:70]([N:72]([CH3:74])[CH3:73])=[O:71])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][CH2:25][O:26][C:75]3[CH:76]=[CH:77][CH:78]=[C:68]([O:67][CH2:60][C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[C:69]=3[C:70](=[O:71])[N:72]([CH3:73])[CH3:74])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 667505692-benzyloxy-6-hydroxy-N,N-dimethylbenzamideHCID 667506243-Benzyloxy-7-(2-hydroxyethoxy)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 667506293-Benzyloxy-7-[2-(3-benzyloxy-2-dimethylcarbamoylphenoxy)-ethoxy]-naphthalene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-benzyloxy-7-(2-hydroxyethoxy)-naphthalene-2-carboxylic acid methyl ester (239 mg, 0.68 mmol), triphenylphosphine (445 mg, 1.70 mmol) and DIAD (0.334 mL, 1.70 mmol) in THF (10 mL) is stirred at RT for 15 min. Then 2-benzyloxy-6-hydroxy-N,N-dimethylbenzamide (460 mg, 1.70 mmol) in THF (8 mL) is added drop wise and the mixture is stirred at RT for 18 h. The solvent is removed and the residue is purified to give the title compound.

Workup

  1. stirringthe mixture is stirred at RT for 18 h
  2. customThe solvent is removed
  3. customthe residue is purified

Sources & evidence

ORD record
ord-3b6e12bc0ce74a2da526039bcefd612d
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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