Triphenylphosphine → HCID 86722610, compound

HRID 2271499Notes

Reaction equation

HRID 2271499 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[Cl:6][C:7]1[CH:8]=[C:9]([CH:14](O)[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:10]=[CH:11][C:12]=1[Cl:13].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>O1CCCC1>[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]([N:2]2[N:3]=[N:4][CH:5]=[N:1]2)[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594467411-Azetidinecarboxylic acid, 3-[(3,4-dichlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl esterHCID 178418441HCID 178418441, compound

Product 1

HCID 86722610HCID 86722610, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Tetrazole (90.0 mg, 1.28 mmol) was added to tertiary butyl 3-((3,4-dichlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate (200 mg, 0.638 mmol) and triphenylphosphine (335 mg, 1.28 mmol) dissolved in the distilled tetrahydrofuran solution (15.0 mL), and diisopropyl azocarboxylate (0.25 mL, 1.28 mmol) was slowly added thereto at 0° C., and the mixture was stirred at room temperature for one day. The solvent of the reaction mixture was removed by reduced pressure evaporation to obtain a yellow liquid, which was purified by flash chromatography (n-hexane:ethyl acetate (4:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (4:1, v/v)) (yield: 88%, white solid). This white solid was dissolved in 10 mL of methanol solution, and 1 N HCl (3.0 mL) was added thereto, and heated to reflux at 60° C. for one day. Thereafter, the solvent of the reaction mixture was removed by reduced pressure evaporation to obtain the title compound (KHG27280).

Workup

  1. additionwas slowly added
  2. customThe solvent of the reaction mixture was removed by reduced pressure evaporation
  3. customto obtain a yellow liquid, which
  4. customwas purified by flash chromatography (n-hexane:ethyl acetate (4:1
  5. dissolutionThis white solid was dissolved in 10 mL of methanol solution
  6. addition1 N HCl (3.0 mL) was added
  7. temperatureheated
  8. temperatureto reflux at 60° C. for one day
  9. customThereafter, the solvent of the reaction mixture was removed by reduced pressure evaporation

Sources & evidence

ORD record
ord-8a41be24fdcf4e57a2c0c6a2848c75fe
Source dataset
uspto-grants-2015_09
Patent number
US09120771B2

Reaction notes

Loading…