Triphenylphosphine → Ethyl (2R)-2-(4-{1-[3-(4-butylphenyl)propan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoate

HRID 1072711Notes

Reaction equation

HRID 1072711 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][N:14]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O[C@@H:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][N:14]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:20]2[CH:25]=[CH:24][C:23]([O:26][C@H:28]([CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:22][CH:21]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9877619Ethyl phenyllactate, (-)-HCID 223873454-{1-[3-(4-butylphenyl)propan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenol

Product 1

HCID 86759768Ethyl (2R)-2-(4-{1-[3-(4-butylphenyl)propan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoateYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-{1-[3-(4-butylphenyl)propan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenol (880 mg, 2.53 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (492 mg, 2.53 mmol), triphenylphosphine (665 mg, 2.54 mmol) and diethyl azodicarboxylate (442 mg, 2.54 mmol) in toluene (30 ml) was refluxed for 20 hours under heating. The residue was poured into water, extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 440 mg (yield: 33%)

Workup

  1. temperatureunder heating
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate anhydride
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  7. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-b21c142f7c17407bb9ebc7ff3b76dc1b
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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