Triphenylphosphine → ethyl 3-cyclopropyl-3-(3-((N-(2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)-2-nitrophenylsulfonamido)methyl)phenyl)propanoate

HRID 1049424Notes

Reaction equation

HRID 1049424 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]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-:28])=[O:27])(=[O:19])=[O:18])=[CH:12][C:11]=1[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31].[CH:34]1([CH:37]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50]O)[CH:45]=2)[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:36][CH2:35]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH:34]1([CH:37]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50][N: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])=[C:11]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:12]=3)[S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-:28])=[O:27])(=[O:18])=[O:19])[CH:45]=2)[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoateHCID 117759909N-(2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)-2-nitrobenzenesulfonamide

Product 1

HCID 117759657ethyl 3-cyclopropyl-3-(3-((N-(2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)-2-nitrophenylsulfonamido)methyl)phenyl)propanoateYield 96.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)-2-nitrobenzenesulfonamide (892 mg), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (445 mg) and triphenylphosphine (990 mg) in THF (19 mL) was added a 40% solution of diethyl azodicarboxylate in toluene (1.49 mL) at 0° C., and the 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 (NH, ethyl acetate/hexane) to give the title compound (1.22 g) as a colorless gummy substance.

Workup

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

Sources & evidence

ORD record
ord-99791b9212f640bdb0c36ef048628f5d
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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