Acetamide → 3-(4-Methyl-oxazol-2-yl)-azetidine-1-carboxylic acid benzyl ester

HRID 528743Notes

Reaction equation

HRID 528743 reaction equation
O=[C:2]([CH3:21])[CH2:3][O:4][C:5]([CH:7]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:8]1)=O.C([NH2:25])(=O)C.B(F)(F)F.CCOCC>C1(C)C(C)=CC=CC=1>[CH2:14]([O:13][C:11]([N:9]1[CH2:10][CH:7]([C:5]2[O:4][CH:3]=[C:2]([CH3:21])[N:25]=2)[CH2:8]1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 67457562Azetidine-1,3-dicarboxylic acid 1-benzyl ester 3-(2-oxo-propyl)ester

Product 1

HCID 674568413-(4-Methyl-oxazol-2-yl)-azetidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

To 130 mg (0.45 mmol) azetidine-1,3-dicarboxylic acid 1-benzyl ester 3-(2-oxo-propyl)ester in 4 mL xylene were added 132 mg (2.25 mmol) acetamide, 39 μL (0.31 mmol) boron trifluoride etherate and the mixture was heated at 130° C. for 24 hours. After cooling to room temperature and evaporation of the solvent the product was purified by chromatography (silica, hexane-EtOAc 6:4).

Workup

  1. temperatureAfter cooling to room temperature
  2. customevaporation of the solvent the product
  3. customwas purified by chromatography (silica, hexane-EtOAc 6:4)

Sources & evidence

ORD record
ord-a4e57b6a5c3c4b609925e4e961a17874
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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