Benzoyl chloride → HCID 86722608, compound

HRID 2271496Notes

Reaction equation

HRID 2271496 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]([OH:30])[CH:19]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]2)[CH:14]=[CH:15][C:16]=1[Cl:17].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:30][CH:18]([C:13]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([Cl:10])[CH:12]=1)[CH:19]1[CH2:20][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:22]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 594467411-Azetidinecarboxylic acid, 3-[(3,4-dichlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86722608HCID 86722608, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.1 mL, 1.20 mmol) and DMAP (5 mg, 0.03 mmol) were slowly added to 15 mL of tertiary butyl 3-((3,4-dichlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate (100 mg, 0.302 mmol) and triethylamine (0.07 mL, 0.482 mmol) dissolved in the distilled methylene chloride solution at 0° C., and the mixture was stirred at room temperature for one day. The reaction mixture was extracted with methylene chloride (3*30 mL), and the organic layer was washed with a 1 N HCl aqueous solution and distilled water once, respectively and dried over anhydrous magnesium sulfate. The solvent was removed by reduced pressure evaporation to obtain a colorless liquid, which was purified by flash chromatography (n-hexane:ethyl acetate (2:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (2:1, v/v)).

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride (3*30 mL)
  2. washthe organic layer was washed with a 1 N HCl aqueous solution
  3. distillationdistilled water once
  4. dry with materialrespectively and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by reduced pressure evaporation
  6. customto obtain a colorless liquid, which
  7. customwas purified by flash chromatography (n-hexane:ethyl acetate (2:1

Sources & evidence

ORD record
ord-5fd379ffd7c042df9003ec3c94905fb5
Source dataset
uspto-grants-2015_09
Patent number
US09120771B2

Reaction notes

Loading…