Carbonate Ion → 3-[2-(trifluoromethyl)-4'-fluorobenzhydryloxy]-N-[(S)-alpha-methyl-benzyl]azetidine-1-carboxamide

HRID 1785729Notes

Reaction equation

HRID 1785729 reaction equation
Cl.[F:2][C:3]([F:24])([F:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]([O:14][CH:15]1[CH2:18][NH:17][CH2:16]1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[CH3:29][C@H:30]([N:37]=[C:38]=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[F:24][C:3]([F:2])([F:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]([O:14][CH:15]1[CH2:18][N:17]([C:38]([NH:37][C@@H:30]([CH3:29])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])[CH2:16]1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 2724173(S)-(-)-1-Phenylethyl isocyanateHCID 689056553-[2-(Trifluoromethyl)-4'-fluorobenzhydryloxy]azetidine hydrochloride

Product 1

HCID 111673563-[2-(trifluoromethyl)-4'-fluorobenzhydryloxy]-N-[(S)-alpha-methyl-benzyl]azetidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (150 mg, 0.42 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 475 mg, 1.26 mmol), molecular sieves and (S)-α-methylbenzyl isocyanate (60 μL, 0.42 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 (24 mL), then evaporated to afford the desired product as a colourless glass which gave a white solid on scratching (136 mg, 69%).

Workup

  1. washThe sample was eluted with DCM (24 mL)
  2. customevaporated

Sources & evidence

ORD record
ord-3ad871b074964553af5f26611c5407c1
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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