Nitrogen → HCID 69508328, compound

HRID 1375687Notes

Reaction equation

HRID 1375687 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[CH2:19][OH:20])[CH:12]=1)(=[O:3])[CH3:2].O[C:27]1[C:28]([OH:37])=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N#N.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:4][CH2:5][C:6]1[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[CH2:19][O:20][C:34]2[CH:35]=[CH:36][CH:27]=[C:28]([OH:37])[C:29]=2[C:30]([O:32][CH3:33])=[O:31])[CH:12]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 75484Methyl 2,3-DihydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 69508170HCID 69508170, compound

Product 1

HCID 69508328HCID 69508328, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-((acetyloxy)methyl)-5-{3-((1E)-3-hydroxyprop-1-enyl)phenyl}isoxazole-3-carboxylate (960 mg, 2.78 mmol) in THF (14 mL) was added methyl dihydroxybenzoate (934 mg, 5.57 mmol) and PPh3 (1.46 g, 5.57 mmol). After purging the vessel with N2, diethyazodicarboxylate (968 mg, 5.57 mmol) was added. The mixture was stirred for 16 hours, concentrated under vacuo and the residue purified by column chromatography (0–40% ethyl acetate in hexanes) to provide the titled compound (590 mg, 43%).

Workup

  1. additionwas added
  2. concentrationconcentrated under vacuo
  3. customthe residue purified by column chromatography (0–40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6b6dcae87ec846feb30ee90565c6c5c4
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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