Chloroacetyl chloride → N-((1-Benzhydryl-3-hydroxyazetidin-3-yl)methyl)-2-chloroacetamide

HRID 1689269Notes

Reaction equation

HRID 1689269 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH2:7][C:8]1([OH:25])[CH2:11][N:10]([CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH:12]([N:10]1[CH2:9][C:8]([CH2:7][NH:6][C:3](=[O:4])[CH2:2][Cl:1])([OH:25])[CH2:11]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 206685333-(Aminomethyl)-1-(diphenylmethyl)azetidin-3-ol

Product 1

HCID 57988954N-((1-Benzhydryl-3-hydroxyazetidin-3-yl)methyl)-2-chloroacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Chloroacetyl chloride (0.846 mL) was added dropwise over 30 minutes to a vigorously stirred mixture of 3-(aminomethyl)-1-benzhydrylazetidin-3-ol (example 33, step c) (2.1 g) in ethyl acetate (100 mL) and potassium carbonate (3.03 g) in water (100 mL) at 0° C. The mixture was stirred for a further 30 minutes at 0° C. and then extracted with ethyl acetate, the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 2.6 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-bc7b7bf4f97e435294a334141a726012
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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