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

HRID 471038Notes

Reaction equation

HRID 471038 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-ea65ba7375d449bc9f06c4bca9c77645
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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