Triphenylphosphine → HCID 66892278, compound

HRID 456230Notes

Reaction equation

HRID 456230 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23]O)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[CH3:26][C:27]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][C:14]=2[CH2:23][N:29]2[C:28](=[O:33])[C:27]([CH3:26])([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:31][C:30]2=[O:32])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 930435-Methyl-5-phenylhydantoinHCID 66606415(2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66892278HCID 66892278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (2′-hydroxymethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.158 g, 0.44 mmol), 5-methyl-5-phenylhydantoin (0.102 g, 0.53 mmol), and triphenylphosphine (0.141 g, 0.53 mmol) in THF (3 mL) was added diisopropyl azodicarboxylate (0.1 mL, 0.53 mmol), and the reaction was stirred overnight at room temperature. Once no starting material was seen by analytical LCMS, the mixture was concentrated and purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c43cced59fb3423db08d157c1b1eb10e
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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