Potassium Carbonate → 3-(3-Nitro-5-trifluoromethyl-phenoxymethyl)-azetidine-1-carboxylic Acid Benzyl Ester

HRID 887660Notes

Reaction equation

HRID 887660 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:21]([O:28][C:29]([N:31]1[CH2:34][CH:33]([CH2:35]O)[CH2:32]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:28][C:29]([N:31]1[CH2:34][CH:33]([CH2:35][O:14][C:6]2[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:32]1)=[O:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 448291173-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

Product 1

HCID 689100943-(3-Nitro-5-trifluoromethyl-phenoxymethyl)-azetidine-1-carboxylic Acid Benzyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitro-5-trifluoromethyl-phenol (750 mg, Step C), K2CO3 (3 eq., 1.5 g) and 3-hydroxymethyl-azetidine-1-carboxylic acid benzyl ester (1.1 eq., 1.2 g) in DMF was heated to 80 C for 1 h. The solution was cooled to RT then filtered and concentraced under vacuum. The residue was dissolved in CH2Cl2 and washed with H2O twice, followed by brine. The organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography using 5% MeOH/CH2Cl2 to provide the desired compound as a colorless solid.

Workup

  1. temperaturewas heated to 80 C for 1 h
  2. filtrationthen filtered
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with H2O twice
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fbe42f6774634beba8b60ee059e4bea6
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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