Propionyl chloride → HCID 21904438, compound

HRID 1839201Notes

Reaction equation

HRID 1839201 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C(Cl)Cl>[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:23])[CH2:21][CH3:22])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 21904405HCID 21904405, compound

Product 1

HCID 21904438HCID 21904438, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-Boc-Azetidine-3-ylmethyl)aniline 48 (218.6 mg, 0.791 mmol) and piperidinomethyl polystyrene resin (250 mg) in 2 mL of dry CH2Cl2 was added propionyl chloride (77 μL, 1 eq.) at room temperature. After being shaken at room temperature overnight, the reaction mixture was passed through an aminopropyl NH2 cartridge and washed with CH2Cl2 Removal of CH2Cl2 afforded N-(1-Boc-azetidine-3-ylmethyl)-N-phenylpropionamide 49 (241 mg, 96%).

Workup

  1. washwashed with CH2Cl2 Removal of CH2Cl2

Sources & evidence

ORD record
ord-f37d490923064383a431d04a1a6ee626
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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