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

HRID 1072707Notes

Reaction equation

HRID 1072707 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.O[C@@H:24]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26].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>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[C:16]2[CH:17]=[CH:18][C:19]([O:22][C@H:24]([CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:21]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9877619Ethyl phenyllactate, (-)-HCID 223874754-[1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl]phenol

Product 1

HCID 86588891Ethyl (2R)-2-(4-{1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoateYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl]phenol (3.00 g, 8.42 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.96 g, 10.1 mmol) and triphenylphosphine (2.65 g, 10.1 mmol) in toluene (30 ml) was added diethyl azodicarboxylate (1.76 g, 10.1 mmol) and refluxed for 20 hours under heating. The insoluble matter was filtered out and the filtrate was diluted with ethyl acetate. The obtained solution was washed with water and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 2.40 g (yield: 54.0%)

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureunder heating
  3. filtrationThe insoluble matter was filtered out
  4. additionthe filtrate was diluted with ethyl acetate
  5. washThe obtained solution was washed with water
  6. dry with materialdried over magnesium sulfate anhydride
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  9. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-9dd854018f0b40f189b12455cbdd0f1c
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

Loading…