Triphenylphosphine → HCID 58047192, compound

HRID 1888785Notes

Reaction equation

HRID 1888785 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:24]=[CH:23][C:13]3[CH:14]=[C:15]([CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[O:16][C:12]=3[CH:11]=2)=[CH:4][CH:3]=1.[CH:25]1([CH2:28][CH2:29]O)[CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>C1COCC1>[CH:25]1([CH2:28][CH2:29][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]3[CH:24]=[CH:23][C:13]4[CH:14]=[C:15]([CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[O:16][C:12]=4[CH:11]=3)=[CH:6][CH:7]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1376422-Cyclopropylethan-1-olHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 58047041HCID 58047041, compound

Product 1

HCID 58047192HCID 58047192, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(1-{6-[2-(4-hydroxyphenyl)ethyl]-1-benzofuran-2-yl}ethyl)acetamide (50.0 mg, 0.154 mmol) obtained in Example 165, 2-cyclopropylethanol (0.0529 mL, 0.616 mmol) and triphenylphosphine (161 mg, 0.616 mmol) in THF (1 mL) were added di(methoxyethyl) azodicarboxylate (144 mg, 0.616 mmol), and the mixture was stirred at room temperature for 30 min. The reaction mixture was directly purified by basic silica gel column chromatography (hexane:ethyl acetate=1:0 to 2:3), and the solvent was evaporated. The residue was triturated with a small amount of diisopropyl ether and hexane to give the title compound (25.9 mg, yield 43%) as a white solid.

Workup

  1. customThe reaction mixture was directly purified by basic silica gel column chromatography (hexane:ethyl acetate=1:0 to 2:3)
  2. customthe solvent was evaporated
  3. customThe residue was triturated with a small amount of diisopropyl ether and hexane

Sources & evidence

ORD record
ord-48aefe7d95014f79943da442012cc061
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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