4-Isopropoxy-3-(methoxymethyl)benzoic acid → tert-butyl N-(3-{5-[4-isopropoxy-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate

HRID 219976Notes

Reaction equation

HRID 219976 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[CH2:14][O:15][CH3:16])([CH3:3])[CH3:2].[NH2:17][C:18](=[N:36]O)[C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][CH:35]=1)[CH2:22][N:23]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:24]>>[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:36]=[C:18]([C:19]3[CH:20]=[C:21]([CH:33]=[CH:34][CH:35]=3)[CH2:22][N:23]([CH3:24])[CH2:25][C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[N:17]=2)=[CH:7][C:6]=1[CH2:14][O:15][CH3:16])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 594957854-Isopropoxy-3-(methoxymethyl)benzoic acidHCID 72307500Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetate

Product 1

HCID 67528677tert-butyl N-(3-{5-[4-isopropoxy-3-(methoxymethyl)phenyl]-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 56 (201.83 mg; 0.90 mmol) and Intermediate 51 (220 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 slightly yellow solid. 1H NMR (CDCl3) δ 8.25 (d, J=2.2 Hz, 1H), 8.12 (d, J=1.7 Hz, 1H), 8.09 (d, J=2.2 Hz, 1H), 8.06 (br s, 1H), 7.57-7.55 (m, 1H), 7.47 (t, J=7.5 Hz, 1H), 6.98 (d, J=8.9 Hz, 1H), 4.70 (quint., J=6.1 Hz, 1H), 4.54 (s, 2H), 3.78 (s, 2H), 3.50 (s, 3H), 3.23 (s, 2H), 2.41 (s, 3H), 1.50 (s, 9H), 1.40 (d, J=6.0 Hz, 6H). HPLC (Method A) Rt 4.96 min (Purity: 100.0%).

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-9e19a398a36c4523b5a3a715e1d7f596
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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