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

HRID 219975Notes

Reaction equation

HRID 219975 reaction equation
[NH2:1][C:2](=[N:21][OH:22])[C:3]1[CH:4]=[CH:5][C:6]([F:20])=[C:7]([CH:19]=1)[CH2:8][N:9]([CH3:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH2:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([C:37](O)=O)=[CH:33][C:32]=1[CH2:40][O:41][CH3:42])[CH3:24]>>[CH2:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:22][N:21]=[C:2]([C:3]3[CH:4]=[CH:5][C:6]([F:20])=[C:7]([CH:19]=3)[CH2:8][N:9]([CH3:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:1]=2)=[CH:33][C:32]=1[CH2:40][O:41][CH3:42])[CH3:24]

Participants

3

Reactant 2

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 72307469tert-butyl N-{5-[amino(hydroxyimino)methyl]-2-fluorobenzyl}-N-methylglycinate

Product 1

HCID 67528793tert-butyl N-(5-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzyl)-N-methylglycinate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 60 (256.87 mg; 0.83 mmol) and Intermediate 36 (202.74 mg; 0.75 mmol). The reaction mixture was filtered through a SPE NH2 column (2 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 8.42 (d, J=1.4 Hz, 1H), 8.26 (dd, J=7.0, 2.1 Hz, 1H), 8.18-8.09 (m, 2H), 7.41-7.34 (m, 3H), 7.29-7.23 (m, 1H), 7.19 (t, J=9.0 Hz, 1H), 7.12-7.10 (m, 1H), 4.27-4.17 (m, 2H), 3.90 (s, 2H), 3.38 (s, 3H), 3.28 (s, 2H), 2.47-2.29 (m, 5H), 1.51 (s, 9H), 1.05 (t, J=7.5 Hz, 3H). LC/MS (Method B): 546.3 (M+H)+. HPLC (Method A) Rt 5.04 min (Purity: 99.5%).

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. 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-2be70e08c84841008be93f573ce410a1
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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