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

HRID 1958818Notes

Reaction equation

HRID 1958818 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]([CH2:43][CH3:44])[CH:42]=1)[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]=[C:41]([CH2:43][CH3:44])[CH:42]=[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 866505073-Ethyl-5-formylbenzoic acidHCID 87208794HCID 87208794, compoundHCID 178436630HCID 178436630, compound

Product 1

HCID 86650516N-((S)-3-{2-ethyl-4-[5-(3-formyl-5-ethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 34.1%

Procedure

The title compound (538 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-ethyl-benzoic acid (600 mg, 3.37 mmol) and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (1096 mg, 3.37 mmol). LC-MS**: tR=0.74 min; [M+1]+=468.26; 1H NMR (D6-DMSO): δ 1.24 (t, J=7.5 Hz, 3H), 1.30 (t, J=7.5 Hz, 3H), 2.36 (s, 3H), 2.71-2.78 (m, 5H), 2.88 (q, J=7.8 Hz, 2H), 2.90 (s, 3H), 3.21-3.28 (m, 1H), 3.41-3.48 (m, 1H), 3.72-3.82 (m, 2H), 3.84 (s, 2H), 3.94-4.01 (m, 1H), 5.31 (br s, 1H), 5.55 (br s, 1H), 7.70 (t, J=6.0 Hz, 1H), 7.83 (s, 2H), 7.96 (s, 1H), 8.10 (s, 1H), 8.35 (s, 1H), 8.52 (s, 1H), 10.16 (s, 1H).

Sources & evidence

ORD record
ord-217f5ad485ba4a8b919be7547df1db22
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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