5-Formyl-4-methylthiophene-2-carboxylic acid → N-((S)-3-{2-Ethyl-4-[5-(5-formyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide
Reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1[CH3:11])=[O:2].[CH2:12]([C:14]1[CH:29]=[C:28]([C:30](=[NH:33])[NH:31]O)[CH:27]=[C:26]([CH3:34])[C:15]=1[O:16][CH2:17][C@@H:18]([OH:25])[CH2:19][NH:20][C:21](=[O:24])[CH2:22][OH:23])[CH3:13]>>[CH2:12]([C:14]1[CH:29]=[C:28]([C:30]2[N:33]=[C:8]([C:6]3[S:7][C:3]([CH:1]=[O:2])=[C:4]([CH3:11])[CH:5]=3)[O:10][N:31]=2)[CH:27]=[C:26]([CH3:34])[C:15]=1[O:16][CH2:17][C@@H:18]([OH:25])[CH2:19][NH:20][C:21](=[O:24])[CH2:22][OH:23])[CH3:13]Participants
3
Procedure
The title compound is prepared according to Method A starting from 5-formyl-4-methyl-thiophene-2-carboxylic acid and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide; LC-MS: tR=0.92 min; [M+1]+=460.17; 1H NMR δ 1.22 (t, J=7.5 Hz, 3H), 2.35 (s, 3H), 2.65 (s, 3H), 2.73 (q, J=7.5 Hz, 2H), 3.20-3.28 (m, 1H), 3.39-3.47 (m, 1H), 3.70-3.80 (m, 2H), 3.84 (d, J=5.5 Hz, 2H), 3.92-4.00 (m, 1H), 5.30 (d, J=5.3 Hz, 1H), 5.54 (t, J=5.8 Hz, 1H), 7.69 (t, J=5.5 Hz, 1H), 7.76 (s, 2H), 8.07 (s, 1H), 10.17 (s, 1H).
Sources & evidence
- ORD record
- ord-539ef1e674f64f46af6752f0f8b8660a
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148410B2
Reaction notes
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