Triphenylphosphine → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-3-(1-methoxy-3,3-dimethylbutyl)-[1,1'-biphenyl]-4-yl)oxy)methyl)phenyl)propanoate

HRID 1049445Notes

Reaction equation

HRID 1049445 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH:17]([O:23][CH3:24])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:44]1([CH:47]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60]O)[CH:55]=2)[CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:46][CH2:45]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH:44]1([CH:47]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60][O:16][C:13]3[CH:14]=[CH:15][C:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[F:1])=[CH:11][C:12]=3[CH:17]([O:23][CH3:24])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH:55]=2)[CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1177597322'-Fluoro-5'-methoxy-3-(1-methoxy-3,3-dimethylbutyl)-[1,1'-biphenyl]-4-olHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate

Product 1

HCID 117760178Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-3-(1-methoxy-3,3-dimethylbutyl)-[1,1'-biphenyl]-4-yl)oxy)methyl)phenyl)propanoateYield 78.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2′-fluoro-5′-methoxy-3-(1-methoxy-3,3-dimethylbutyl)-[1,1′-biphenyl]-4-ol (290 mg) in THF (5.0 mL) were added triphenylphosphine (343 mg), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (325 mg) and a 40% solution of diethyl azodicarboxylate in toluene (600 μL), and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (385 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-06df2f6a51ee4e50b43a2503b9828a97
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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