Triphenylphosphine → HCID 69420233, compound

HRID 350042Notes

Reaction equation

HRID 350042 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:38]=[CH:37][C:17]([CH2:18][N:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[CH:20]2)=[CH:16][CH:15]=1.[CH3:39][C:40]1[O:44][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[N:42][C:41]=1[CH2:51][CH2:52]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1.C1(C)C=CC=CC=1>[CH3:39][C:40]1[O:44][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[N:42][C:41]=1[CH2:51][CH2:52][O:13][C:14]1[CH:38]=[CH:37][C:17]([CH2:18][N:19]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:21]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:20]2)=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 23024736Ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

Product 1

HCID 69420233HCID 69420233, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A toluene solution (5.66 g) of 40% diethyl azodicarboxylate was added dropwise slowly to a mixture of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (2.84 g), 2-(5-methyl-2-phenyl-4-oxazolyl)ethanol (2.48 g), triphenylphosphine (3.31 g) and tetrahydrofuran (25 ml) at room temperature. After the above solution was stirred at room temperature for 2 hours, the reaction solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography, and an oily substance was obtained from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). A mixture of the oily substance obtained, 1N aqueous sodium hydroxide solution (15 ml), tetrahydrofuran (15 ml) and ethanol (15 ml) was stirred at room temperature for 3 hours and the organic solvent was removed under reduced pressure. After adding water, the residue was acidified by adding 1N hydrochloric acid. The colorless crystals obtained were collected by filtration to yield 3-[1-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid (2.72 g, yield: 57%). This was recrystallized from ethanol-water. Melting point: 147–148° C.

Workup

  1. customthe reaction solvent was removed under reduced pressure
  2. customan oily substance was obtained from the fraction
  3. washeluted with ethyl acetate-hexane (1:4, volume ratio)
  4. additionA mixture of the oily substance
  5. customobtained
  6. customthe organic solvent was removed under reduced pressure
  7. additionAfter adding water
  8. additionby adding 1N hydrochloric acid
  9. customThe colorless crystals obtained
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-51af693e991c4a05bc0873acd793b08e
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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