Trifluoroacetic acid → HCID 11625833, compound

HRID 2253039Notes

Reaction equation

HRID 2253039 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[O:25][N:24]=3)=[C:17]([Cl:36])[CH:16]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:36][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[N:27]=[C:26]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[O:25][N:24]=1)[CH2:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67073371HCID 67073371, compound

Product 1

HCID 11625833HCID 11625833, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 0.30 g (0.6 mmol) (R)-2-{3-chloro-4-[5-(4-methoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-benzyl}-morpholine-4-carboxylic acid tert-butyl ester in 3 mL dichloromethane was cooled to 0° C. and treated with 1.5 mL (19.6 mmol) trifluoroacetic acid. The cooling bath was removed and the solution stirred at room temperature for 1 h. The volatile components were evaporated and the residue dissolved in dichloromethane and extracted with 1N aqueous sodium hydroxide solution. The organic layer was washed with brine, dried over magnesium sulfate, evaporated and dried under high vacuum to give 0.23 g (95%) of the product as colorless oil.

Workup

  1. customThe cooling bath was removed
  2. customThe volatile components were evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. extractionextracted with 1N aqueous sodium hydroxide solution
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-2950aaa088174efe80648d9f3799d19c
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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