3-Formyl-4-ethyl-benzoic acid → N-((S)-3-{2-ethyl-4-[5-(3-formyl-4-ethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1958815Notes

Reaction equation

HRID 1958815 reaction equation
C(C1C=C(C2ON=C(C3C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=3)N=2)C=CC=1)=O.[CH:32]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[CH2:43][CH3:44])[C:37]([OH:39])=O)=[O:33].[CH2:45]([C:47]1[CH:62]=[C:61]([C:63](=[NH:66])[NH:64]O)[CH:60]=[C:59]([CH3:67])[C:48]=1[O:49][CH2:50][C@@H:51]([OH:58])[CH2:52][NH:53][C:54](=[O:57])[CH2:55][OH:56])[CH3:46]>>[CH2:45]([C:47]1[CH:62]=[C:61]([C:63]2[N:66]=[C:37]([C:36]3[CH:40]=[CH:41][C:42]([CH2:43][CH3:44])=[C:34]([CH:32]=[O:33])[CH:35]=3)[O:39][N:64]=2)[CH:60]=[C:59]([CH3:67])[C:48]=1[O:49][CH2:50][C@@H:51]([OH:58])[CH2:52][NH:53][C:54](=[O:57])[CH2:55][OH:56])[CH3:46]

Participants

4

Reactant 3

HCID 866505093-Formyl-4-ethyl-benzoic acidHCID 87208794HCID 87208794, compoundHCID 178436630HCID 178436630, compound

Product 1

HCID 86650513N-((S)-3-{2-ethyl-4-[5-(3-formyl-4-ethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 24.7%

Procedure

The title compound (233 mg) is prepared in analogy to rac-N-(3-{4-[5-(3-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide, starting from 3-formyl-4-ethyl-benzoic acid (360 mg, 2.02 mmol) and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (657 mg, 2.02 mmol). LC-MS**: tR=0.72 min; [M+1]+=468.21; 1H NMR (D6-DMSO): δ 1.23 (t, J=7.5 Hz, 3H), 1.26 (t, J=7.5 Hz, 3H), 2.35 (s, 3H), 2.74 (q, J=7.5 Hz, 2H), 3.17 (q, J=7.3 Hz, 2H), 3.21-3.29 (m, 1H), 3.40-3.48 (m, 1H), 3.70-3.80 (m, 2H), 3.84 (d, J=5.8 Hz, 2H), 3.93-4.01 (m, 1H), 5.32 (d, J=5.0 Hz, 1H), 5.56 (t, J=5.8 Hz, 1H), 7.68-7.73 (m, 2H), 7.81 (s, 2H), 8.37 (dd, J=8.0, 1.8 Hz, 1H), 8.61 (d, J=1.8 Hz, 1H), 10.38 (s, 1H).

Sources & evidence

ORD record
ord-f2924c1304b54a26b0c39fe433c5e6d9
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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