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

HRID 923606

Reaction equation

HRID 923606 reaction equation
C(OC([NH:8][C:9]1[CH:50]=[CH:49][C:12]([C:13]([N:15]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][N:26]=[C:25]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)[N:24]=3)=[CH:19][CH:18]=2)=[O:14])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:8][C:9]1[CH:50]=[CH:49][C:12]([C:13]([N:15]([CH2:41][C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[O:27][N:26]=[C:25]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)[N:24]=3)=[CH:21][CH:22]=2)=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 71111627tert-butyl 2-(4-((tert-butoxycarbonyl)amino)-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate

Product 1

HCID 89284665tert-butyl 2-(4-amino-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetateYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 8. To a stirred solution of tert-butyl 2-(4-((tert-butoxycarbonyl)amino)-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate INT-63 (659 mg, 0.977 mmol) in DCM (15 mL) was added TFA (752 μL, 9.77 mmol) at room temperature. After 2 h additional TFA (752 μL, 9.77 mmol) was added and the reaction mixture stirred for a further 3 h at room temperature. The reaction mixture was diluted with toluene (20 mL) and the solvent removed in vacuo. The residue was diluted with EA (100 mL) and washed with NaHCO3 (30 mL). The organics were concentrated in vacuo and the crude product was purified by chromatography (EA/hexanes) to afford 284 mg (50%) of tert-butyl 2-(4-amino-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate INT-64 as an off-white powder. LCMS-ESI (m/z) calculated for C35H34N4O4: 574; found 519 [M-t-Bu+H]+, 573 [M−H]−, tR=3.12 min (Method 10).

Workup

  1. customPrepared
  2. customthe solvent removed in vacuo
  3. additionThe residue was diluted with EA (100 mL)
  4. washwashed with NaHCO3 (30 mL)
  5. concentrationThe organics were concentrated in vacuo
  6. customthe crude product was purified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-8e64073729534d05a4d7f99cbc840817
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Linked notes

Loading…