Triphenylphosphine → HCID 66643519, compound

HRID 1807530Notes

Reaction equation

HRID 1807530 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[N:6][CH:5]=1.[CH3:12][C:13]1[O:17][N:16]=[C:15]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:14]=1[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:24][C:14]2[C:15]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:16][O:17][C:13]=2[CH3:12])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66643720HCID 66643720, compoundHCID 178498304HCID 178498304, compound

Product 1

HCID 66643519HCID 66643519, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-hydroxy-nicotinic acid methyl ester (1.67 g, 10.9 mmol) and [5-methyl-3-(tetrahydro-pyran-4-yl)-isoxazol-4-yl]-methanol (2.15 g, 10.9 mmol) in THF (55 mL) at 5° C. under argon was added triphenylphosphine (10.6 g, 39 mmol), then diisopropyl azodicarboxylate (40%, 6.5 mL, 14.2 mmol) was added dropwise. The reaction mixture was warmed to room temperature for 2 h. The reaction mixture was then extracted with tert-butyl methyl ether, and washed with aqueous HCl (2 N) and the organic extract washed with water, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:0 to 1:1) afforded the title compound (1.31 g, 36%) as a white solid. MS: m/e=333.2 [M+H]+.

Workup

  1. extractionThe reaction mixture was then extracted with tert-butyl methyl ether
  2. washwashed with aqueous HCl (2 N)
  3. extractionthe organic extract
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (silica, heptane:ethyl acetate=1:0 to 1:1)

Sources & evidence

ORD record
ord-2689947856e94648812e2207bc3bf12d
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

Loading…