3-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzyl]-benzonitrile → 1-(2-hydroxy-3-propyl-4-{4-[3-(1H-tetrazol-5-yl)-benzyl]-benzyloxy}-phenyl)-ethanone

HRID 1161071Notes

Reaction equation

HRID 1161071 reaction equation
F[CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)[CH:25]=1)[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=2[CH2:19][CH2:20][CH3:21])=[CH:5][CH:4]=1.C(C1C=CC(OCC2C=CC(CC3C=C(C=CC=3)C#N)=CC=2)=C(CCC)C=1O)(=O)C>>[OH:18][C:11]1[C:10]([CH2:19][CH2:20][CH3:21])=[C:9]([O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[NH:34][N:33]=[N:32][N:31]=4)[CH:25]=3)=[CH:23][CH:22]=2)[CH:14]=[CH:13][C:12]=1[C:15](=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 666995873-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzyl]-benzonitrileHCID 1784396501-[4-(4-{fluoro-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

Product 1

HCID 1784396461-(2-hydroxy-3-propyl-4-{4-[3-(1H-tetrazol-5-yl)-benzyl]-benzyloxy}-phenyl)-ethanoneYield 58%

Procedure

The title compound is prepared in a similar manner to 1-[4-(4-{fluoro-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone employing 3-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzyl]-benzonitrile. The crude product is purified via reversed phase C18 preparative chromatography over 8 runs to provide the title compound as a tan solid (6.3 g, 58%). 1H NMR (DMSO-d6) δ 12.86 (s, 1H), 7.96 (s, 1H), 7.86-7.89 (m, 1H), 7.81 (d, 1H), 7.48-7.58 (m, 2H), 7.33-7.42 (m, 4H), 6.73 (d, 1H), 5.23 (s, 2H), 4.08 (s, 2H), 2.56-2.61 (m, 5H), 1.45-1.53 (m, 2H), 0.88 (t, 3H). LCMS M−1 441.

Workup

  1. customThe crude product is purified via reversed phase C18 preparative chromatography over 8 runs

Sources & evidence

ORD record
ord-237162174e844e6baf2354fb3a7ced83
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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