Azetidine → Methyl 3-(azetidin-1-ylsulfonyl)-5-(trifluoromethyl)benzoate

HRID 878283Notes

Reaction equation

HRID 878283 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3].CC[N:21]([CH:25]([CH3:27])C)[CH:22](C)C.N1CCC1.[NH4+].[Cl-]>C(Cl)Cl.CCOC(C)=O>[N:21]1([S:2]([C:5]2[CH:6]=[C:7]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3])[CH2:22][CH2:27][CH2:25]1

Participants

7

Reactant 4

HCID 10422AzetidineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 62631505Methyl 3-(chlorosulfonyl)-5-(trifluoromethyl)benzoate

Product 1

HCID 70663263Methyl 3-(azetidin-1-ylsulfonyl)-5-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-(chlorosulfonyl)-5-(trifluoromethyl)benzoate (0.3 g, 991 μmol; Buttpark Ltd.) in CH2Cl2 (1 mL) were added DIPEA (192 mg, 260 μL, 1.49 mmol) and azetidine (62.3 mg, 73.5 μL, 1.09 mmol). The clear, light yellow solution was stirred at room temperature for 4 hours and then poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were dried over MgSO4, filtered, and evaporated. Light brown solid (0.316 g; 98%). MS (EI): m/z=323 [M].

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-12f976c8513b4843b9db865cfd623d85
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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