Trifluoroacetic acid → Methyl 2-((4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)amino)acetate

HRID 923621Notes

Reaction equation

HRID 923621 reaction equation
C(OC([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)=[CH:28][CH:27]=3)[O:23][N:22]=2)=[CH:17][CH:16]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:38][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:28]=[CH:27][C:26]([C:24]3[O:23][N:22]=[C:21]([C:18]4[CH:19]=[CH:20][C:15]([CH2:14][NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:16][CH:17]=4)[N:25]=3)=[CH:31][CH:30]=2)=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71078187Methyl 2-((tert-butoxycarbonyl)(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)amino)acetate

Product 1

HCID 71112506Methyl 2-((4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)amino)acetateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 8. To a stirring solution of methyl 2-((tert-butoxycarbonyl)(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)amino)acetate INT-76 (518 mg, 1.01 mmol) in DCM (10 mL) was added TFA (1 mL) at room temperature. After 2 h the reaction mixture was evaporated to dryness. The crude product was purified by chromatography, eluting with 0.7 M ammonia in MeOH/DCM. The mixture was concentrated in vacuo to afford 272 mg (65%) of methyl 2-((4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)amino)acetate INT-77 as a white solid. LCMS-ESI (m/z) calculated for C25H23N3O3: 413; found 414 [M+H]+, tR=1.89 min (Method 10). Compound 495 was prepared from INT-77 and INT-23 using General Procedures 6 then 9. Compound 498 was prepared from INT-77 and INT-15 using General Procedures 6 then 9.

Workup

  1. customPrepared
  2. customAfter 2 h the reaction mixture was evaporated to dryness
  3. customThe crude product was purified by chromatography
  4. washeluting with 0.7 M ammonia in MeOH/DCM
  5. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-abb4bdb5cda0439cb0faae85fea4be6b
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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