Allyl isocyanate → 3-[2-(trifluoromethyl)-4'-(difluoromethoxy)benzhydryloxy]-N-(allyl)azetidine-1-carboxamide

HRID 1785726Notes

Reaction equation

HRID 1785726 reaction equation
Cl.[F:2][C:3]([F:27])([F:26])[C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH:6]([O:17][CH:18]1[CH2:21][NH:20][CH2:19]1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[CH2:32]([N:35]=[C:36]=[O:37])[CH:33]=[CH2:34]>C(Cl)Cl>[F:27][C:3]([F:2])([F:26])[C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH:6]([O:17][CH:18]1[CH2:21][N:20]([C:36]([NH:35][CH2:32][CH:33]=[CH2:34])=[O:37])[CH2:19]1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:15])[F:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 15123Allyl isocyanateHCID 19660Carbonate IonHCID 866111663-[2-(Trifluoromethyl)-4'-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride

Product 1

HCID 113056123-[2-(trifluoromethyl)-4'-(difluoromethoxy)benzhydryloxy]-N-(allyl)azetidine-1-carboxamideYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride (175) (100 mg, 0.24 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 280 mg, 0.72 mmol), molecular sieves and allyl isocyanate (22 μL, 0.24 mmol). After shaking at ambient temperature for 2 h, the mixture was poured onto a DCM-wet SCX-2 cartridge (2 g). Elution with DCM (20 mL) and evaporation afforded the desired product (68 mg, 61%).

Workup

  1. washElution
  2. customwith DCM (20 mL) and evaporation

Sources & evidence

ORD record
ord-33c04908f03e448ea4d26c7f14b073b1
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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