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

HRID 528747
Notes
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Reaction equation

HRID 528747 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 674562543-(2-Iodo-phenylcarbamoyl)-azetidine-1-carboxylic acid benzyl ester

Product 1

HCID 674541823-Benzooxazol-2-yl-azetidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 4

HCID 313
Hydrochloric Acid
Catalyst
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

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

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with DCM (3×10 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationAfter filtration and evaporation of the solvent the product
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes