Triphenylphosphine → HCID 460106, compound

HRID 2260516Notes

Reaction equation

HRID 2260516 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9](O)([C@H:16]([N:18]([CH2:31][CH2:32][OH:33])[C:19](=[O:30])[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[C@@H:16]([CH3:17])[N:18]([C:19](=[O:30])[C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=2)[CH2:31][CH2:32][O:33]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10458024HCID 10458024, compound

Product 1

HCID 460106HCID 460106, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing (2R*,3R*)-2-[2,4-difluorophenyl]-3-[N-(2-hydroxyethyl)-N-[4-(trifluoromethyl)benzoyl]amino]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (500 mg, 1.03 mmol, obtained in example 3) in THF was treated with diethylazadicarboxylate (262 mg, 1.5 eq) and triphenylphosphine (393 mg, 1.5 eq) at room temperature for 24 h. The volatiles were removed in vacuo and the orange oily residue was purified by flash chromatography to afford the title compound as a colorless wax (209 mg, 45 % yield).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe orange oily residue was purified by flash chromatography

Sources & evidence

ORD record
ord-28bdf4748e644759a9b1bec65ac24b91
Source dataset
uspto-grants-1995_12
Patent number
US05478826

Reaction notes

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