2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid → tert-butyl N-(3-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate

HRID 219972Notes

Reaction equation

HRID 219972 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=O)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2].[NH2:21][C:22](=[N:40][OH:41])[C:23]1[CH:24]=[C:25]([CH:37]=[CH:38][CH:39]=1)[CH2:26][N:27]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:28]>>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:41][N:40]=[C:22]([C:23]3[CH:24]=[C:25]([CH:37]=[CH:38][CH:39]=3)[CH2:26][N:27]([CH3:28])[CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:36])[CH3:34])=[O:31])[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2]

Participants

3

Reactant 2

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 72307500Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetate

Product 1

HCID 67528193tert-butyl N-(3-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 36 and Intermediate 51. The reaction mixture was filtered through a SPE NH2 column (10 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1), affording the title compound as a pale yellow oil. 1H NMR (CDCl3) δ 8.43 (d, J=1.3 Hz, 1H), 8.19-8.16 (m, 2H), 8.11 (d, J=7.5 Hz, 1H), 7.61-7.47 (m, 2H), 7.41-7.34 (m, 3H), 7.29-7.23 (m, 1H), 7.13-7.10 (m, 1H), 4.27-4.18 (m, 2H), 3.80 (s, 2H), 3.33 (s, 3H), 3.24 (s, 2H), 2.48-2.29 (m, 5H), 1.50 (s, 9H), 1.05 (t, J=7.6 Hz, 3H). LC/MS (Method B): 528.3 (M+H)+. HPLC (Method A) Rt 5.05 min (Purity: 98.4%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (10 g)
  3. washrinsed with ACN
  4. customAfter evaporation of the solvents
  5. customthe crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1)

Sources & evidence

ORD record
ord-74ddeaeefece4ed2b6a15987838029e7
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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