Triphenylphosphine → HCID 57238973, compound

HRID 650583Notes

Reaction equation

HRID 650583 reaction equation
[CH3:1][C:2]1[C:3]([CH:16]([OH:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:50][O:51][C:52](=[O:77])[C@@H:53]([NH:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[C:69](=[O:76])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[CH2:54][C:55]1[CH:60]=[CH:59][C:58](O)=[CH:57][CH:56]=1>C1COCC1>[CH3:50][O:51][C:52](=[O:77])[C@@H:53]([NH:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[C:69](=[O:76])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[CH2:54][C:55]1[CH:56]=[CH:57][C:58]([O:18][CH:16]([C:3]2[C:2]([CH3:1])=[CH:11][C:10]3[C:9]([CH3:13])([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]=3[CH:4]=2)[CH3:17])=[CH:59][CH:60]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4983340HCID 4983340, compoundHCID 10667178N-(2-benzoylphenyl)tyrosine methyl ester

Product 1

HCID 57238973HCID 57238973, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-ethanol (184 mg; 0.75 mmol), triphenylphosphine (268 mg; 1.0 mmol), diethyl azodicarboxylate (0.161 ml; 1.0 mmol) and (2S)-2-((2-benzoylphenyl)amino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (190 mg; 0.5 mmol) in THF (10 ml) was stirred at 0° C. for 1.5 hours and for 16 hours at room temperature. The reaction mixture was evaporated and the residue was purified on column chromatography using methylene chloride as eluent. Yield 118 mg.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-e57f933e14b74c98ab4c86b7bdb57da5
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

Loading…