tert-Butyl isocyanate → 3-[2-(trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]-N-(tert-butyl)azetidine-1-carboxamide

HRID 1785718Notes

Reaction equation

HRID 1785718 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH:5]([O:16][CH:17]1[CH2:20][NH:19][CH2:18]1)[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[C:27]([N:31]=[C:32]=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH:5]([O:16][CH:17]1[CH2:20][N:19]([C:32]([NH:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH2:18]1)[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 689037193-[2-(Trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]azetidine

Product 1

HCID 689031113-[2-(trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]-N-(tert-butyl)azetidine-1-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-(methylsulfonyl)benzhydryloxy]azetidine (171) (222 mg, 0.58 mmol) in anhydrous DCM (7 mL) was added molecular sieves and tert-butyl isocyanate (68 μL, 0.58 mmol). After shaking at ambient temperature for 16 h, the mixture was poured onto a DCM-wet SCX-2 cartridge (2 g). Elution with DCM (24 mL) and evaporation afforded the desired product as a pale yellow solid (188 mg, 67%).

Workup

  1. washElution
  2. customwith DCM (24 mL) and evaporation

Sources & evidence

ORD record
ord-71c8e3b4d941402b88d00224e36b95b8
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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