1,10-Phenanthroline → 3-Benzooxazol-2-yl-azetidine-1-carboxylic acid benzyl ester

HRID 528747Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2I)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])(O)=O.[Na+]>COCCOC.Cl.[Cu]I.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]2[O:24][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 195 mg (0.45 mmol) 3-(2-iodo-phenylcarbamoyl)-azetidine-1-carboxylic acid benzyl ester in 4.5 mL DME in a sealed tube under nitrogen were added 291 mg (0.89 mmol) Cs2CO3, 8.1 mg (44.6 μmol) 1,10-phenanthroline, 4.3 mg (22.3 μmol) CuI, and the mixture was heated at 90° C. for 16 hours. After cooling to room temperature, 5 mL H2O was added followed by 4 drops 1 M HCl, 5 mL NaHCO3 and the mixture was extracted with DCM (3×10 mL). The organic layers were combined and dried with Na2SO4. After filtration and evaporation of the solvent the product was purified by preparative HPLC.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with DCM (3×10 mL)
dry with materialdried with Na2SO4
filtrationAfter filtration and evaporation of the solvent the product
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-5cd5c7b326da43ec8c639dd15612c781
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346816B2

Reaction notes

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