Triethylamine → HCID 89525649, compound

HRID 1523293Notes

Reaction equation

HRID 1523293 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])[CH2:15][O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=1)=[O:31]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH:16]([CH3:20])[C:17]([O:19][CH2:29][C:30](=[O:31])[C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:36][CH:37]=2)=[O:18])[CH2:13][O:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 89525535HCID 89525535, compound

Product 1

HCID 89525649HCID 89525649, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-(3-{[(Benzyloxy)carbonyl]amino}oxetan-3-yl)propanoic acid (Preparation 28, 1.5 g, 5.37 mmol) and triethylamine (1.12 mL, 8.06 mmol) were stirred in ethyl acetate (50 mL). 2-Bromo-1-[4-(trifluoromethyl)phenyl]ethanone (1.51 g, 5.64 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound as an oil (2.19 g, 88%).

Workup

  1. washwashed with brine
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af8142f0c30645159601809a3ead340a
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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