Carbonate Ion → 3-[2-(trifluoromethyl)-4'-methoxybenzhydryloxy]-N-(tert-butyl)-azetidine-1-carboxamide

HRID 1785705Notes

Reaction equation

HRID 1785705 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH:5]([O:14][CH:15]1[CH2:18][NH:17][CH2:16]1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[C:29]([N:33]=[C:34]=[O:35])([CH3:32])([CH3:31])[CH3:30]>C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH:5]([O:14][CH:15]1[CH2:18][N:17]([C:34]([NH:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[CH2:16]1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 62412tert-Butyl isocyanateHCID 68903848HCID 68903848, compound

Product 1

HCID 113280313-[2-(trifluoromethyl)-4'-methoxybenzhydryloxy]-N-(tert-butyl)-azetidine-1-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-methoxybenzhydryloxy]azetidine (157) (100 mg, 0.30 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (3.01 mmol/g; 100 mg, 0.30 mmol) and tert-butyl isocyanate (35 μL, 0.30 mmol). The resultant mixture was shaken at ambient temperature for 5 h, after which time it was poured onto a DCM-wetted SCX-2 (1 g) cartridge. The sample was eluted with DCM (6 mL) followed by DCM-MeOH (6 mL), then evaporated. Purification by flash column chromatography [SiO2; ethyl acetate-iso-hexane (35:65→50:50)] afforded the desired product as a colourless glass (90 mg, 70%).

Workup

  1. washThe sample was eluted with DCM (6 mL)
  2. customevaporated
  3. customPurification by flash column chromatography [SiO2; ethyl acetate-iso-hexane (35:65→50:50)]

Sources & evidence

ORD record
ord-976cb1e249184975b23b28ec16e2c9db
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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