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

HRID 1785704Notes

Reaction equation

HRID 1785704 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]12([N:39]=[C:40]=[O:41])[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2>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:40]([NH:39][C:29]23[CH2:38][CH:33]4[CH2:32][CH:31]([CH2:37][CH:35]([CH2:34]4)[CH2:36]2)[CH2:30]3)=[O:41])[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 20599951-IsocyanatoadamantaneHCID 68903848HCID 68903848, compound

Product 1

HCID 114322823-[2-(trifluoromethyl)-4'-methoxybenzhydryloxy]-N-(1-adamantyl)-azetidine-1-carboxamideYield 92%

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 1-adamantyl isocyanate (55 mg, 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. Elution with DCM (6 mL) followed by DCM-MeOH (6 mL), then removal of solvent in vacuo afforded the desired product as a white foam (140 mg, 92%).

Workup

  1. washElution with DCM (6 mL)
  2. customremoval of solvent in vacuo

Sources & evidence

ORD record
ord-b4155ee157044c5eba604188c42dd85b
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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