2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid → Tert-butyl {4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-fluorophenoxy}acetate

HRID 219930Notes

Reaction equation

HRID 219930 reaction equation
[NH2:1][C:2](=[N:19][OH:20])[C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:5]([F:18])[CH:4]=1.[CH3:21][C:22]1[CH:27]=[C:26]([C:28](O)=O)[CH:25]=[CH:24][C:23]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37]>>[CH3:21][C:22]1[CH:27]=[C:26]([C:28]2[O:20][N:19]=[C:2]([C:3]3[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])=[C:5]([F:18])[CH:4]=3)[N:1]=2)[CH:25]=[CH:24][C:23]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37]

Participants

3

Reactant 2

HCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acidHCID 72307490Tert-butyl {4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}acetate

Product 1

HCID 68812572Tert-butyl {4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-fluorophenoxy}acetate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 49 (142.14 mg; 0.50 mmol) and Intermediate 3 (135.76 mg; 0.60 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5), affording the title compound as a colorless oil. LC/MS (Method B): 475.4 (M+H)+. HPLC (Method A) Rt 6.78 min (Purity: 99.3%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5)

Sources & evidence

ORD record
ord-77c294632526471ea714a0e5ac091a18
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

Loading…