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

HRID 1049442Notes

Reaction equation

HRID 1049442 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[F:20])[CH:8]=[CH:9][C:10]=1[OH:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:42]1([CH:45]([C:52]2[CH:57]=[CH:56][CH:55]=[C:54]([CH2:58]O)[CH:53]=2)[CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][CH2:43]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH:42]1([CH:45]([C:52]2[CH:57]=[CH:56][CH:55]=[C:54]([CH2:58][O:11][C:10]3[CH:9]=[CH:8][C:7]([C:12]4[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=4[F:20])=[CH:6][C:5]=3[CH2:4][CH2:3][C:2]([CH3:22])([CH3:21])[CH3:1])[CH:53]=2)[CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][CH2:43]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1177597863-(3,3-Dimethylbutyl)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-4-olHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate

Product 1

HCID 117759575Ethyl 3-cyclopropyl-3-(3-(((3-(3,3-dimethylbutyl)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-4-yl)oxy)methyl)phenyl)propanoateYield 48.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3,3-dimethylbutyl)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-4-ol (200 mg) in THF (5.0 mL) were added triphenylphosphine (260 mg), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (246 mg) and a 40% solution of diethyl azodicarboxylate in toluene (400 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 (170 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-7f179c4f858748519537bf612e268189
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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