Trifluoroacetic acid → HCID 11668184, compound

HRID 270489Notes

Reaction equation

HRID 270489 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][C:11]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]([C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[N:14]=[C:13]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[O:12]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH2:10][C:11]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]([C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[N:14]=[C:13]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[O:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67214914HCID 67214914, compound

Product 1

HCID 11668184HCID 11668184, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[5-(2,5-difluorophenyl)-3-isobutyryl-2-phenyl-2,3-dihydro-[1,3,4]oxadiazol-2-yl]-propyl}-carbamic acid tert-butyl ester (60 mg, 0.123 mmol) in DCM (2 mL) at 0° C. was added TFA (1 mL). After stirring for 10 minutes, the reaction was concentrated and the residue was purified by preparative thin layer chromatography (10:1:0.2 EtOAc/MeOH/30% NH4OH) to provide the desired product (25 mg, 53%). MS ESI (+) m/z 388 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 2H), 7.50 (m, 1H), 7.39 (m, 3H), 7.18 (m, 2H), 3.17 (m, 1H, J=7 Hz), 3.02 (m, 1H), 2.8 (br, 2 H), 2.56 (m, 1H), 1.8 (br, 2H), 1.6 (m, 2H), 1.2 (d, 3H, J=7 Hz), 1.13 (d, 3H, J=7 Hz).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by preparative thin layer chromatography (10:1:0.2 EtOAc/MeOH/30% NH4OH)

Sources & evidence

ORD record
ord-b8963e2038ff46959205ee63361952d6
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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