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

HRID 1958817Notes

Reaction equation

HRID 1958817 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]=[C:41]([CH3:43])[CH:42]=1)[C:37]([OH:39])=O)=[O:33].[CH2:44]([C:46]1[CH:61]=[C:60]([C:62](=[NH:65])[NH:63]O)[CH:59]=[C:58]([CH3:66])[C:47]=1[O:48][CH2:49][C@@H:50]([OH:57])[CH2:51][NH:52][C:53](=[O:56])[CH2:54][OH:55])[CH3:45]>>[CH2:44]([C:46]1[CH:61]=[C:60]([C:62]2[N:65]=[C:37]([C:36]3[CH:40]=[C:41]([CH3:43])[CH:42]=[C:34]([CH:32]=[O:33])[CH:35]=3)[O:39][N:63]=2)[CH:59]=[C:58]([CH3:66])[C:47]=1[O:48][CH2:49][C@@H:50]([OH:57])[CH2:51][NH:52][C:53](=[O:56])[CH2:54][OH:55])[CH3:45]

Participants

4

Reactant 3

HCID 197881733-Formyl-5-methylbenzoic acidHCID 87208794HCID 87208794, compoundHCID 178436630HCID 178436630, compound

Product 1

HCID 86650515N-((S)-3-{2-ethyl-4-[5-(3-formyl-5-methyl-phenyl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 43.4%

Procedure

The title compound (407 mg) was 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-5-methyl-benzoic acid (340 mg, 2.07 mmol) and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (674 mg, 2.07 mmol). LC-MS: tR=0.85 min; [M+1]+=454.11; 1H NMR (D6-DMSO): δ 1.23 (t, J=7.5 Hz, 3H), 2.36 (s, 3H), 2.55 (s, 3H), 2.74 (q, J=7.5 Hz, 2H), 3.20-3.29 (m, 1H), 3.39-3.48 (m, 1H), 3.70-3.81 (m, 2H), 3.84 (d, J=4.8 Hz, 2H), 3.93-4.00 (m, 1H), 5.32 (d, J=4.8 Hz, 1H), 5.56 (t, J=5.0 Hz, 1H), 7.71 (t, J=5.8 Hz, 1H), 7.82 (s, 2H), 8.06 (s, 1H), 8.34 (s, 1H), 8.50 (s, 1H), 10.15 (s, 1H).

Sources & evidence

ORD record
ord-19af350a84354b3eadb1fc601d906905
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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