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

HRID 1785713Notes

Reaction equation

HRID 1785713 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[CH:6]([O:15][CH:16]1[CH2:19][NH:18][CH2:17]1)[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[C:30]12([N:40]=[C:41]=[O:42])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2>C(Cl)Cl>[F:25][C:3]([F:2])([F:24])[C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[CH:6]([O:15][CH:16]1[CH2:19][N:18]([C:41]([NH:40][C:30]23[CH2:39][CH:34]4[CH2:33][CH:32]([CH2:38][CH:36]([CH2:35]4)[CH2:37]2)[CH2:31]3)=[O:42])[CH2:17]1)[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 20599951-IsocyanatoadamantaneHCID 689042363-[2-Trifluoromethyl-4'-(methylthio)benzhydryloxy]azetidine hydrochloride

Product 1

HCID 112378843-[2-(trifluoromethyl)-4'-(methylthio)benzhydryloxy]-N-(1-adamantyl)azetidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) (100 mg, 0.26 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.10 mmol/g; 250 mg, 0.84 mmol) and 1-adamantyl isocyanate (47 mg, 0.26 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which time it was poured onto a DCM-wetted SCX-2 (1 g) cartridge. The sample was eluted with DCM (18 mL), then evaporated to afford the desired product as a white, crystalline solid (70 mg, 51%).

Workup

  1. washThe sample was eluted with DCM (18 mL)
  2. customevaporated

Sources & evidence

ORD record
ord-61bc58caa2094760bb0a142c93d4357d
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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