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

HRID 1958819Notes

Reaction equation

HRID 1958819 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][CH2:44][CH3:45])[CH:42]=1)[C:37]([OH:39])=O)=[O:33].[CH2:46]([C:48]1[CH:63]=[C:62]([C:64](=[NH:67])[NH:65]O)[CH:61]=[C:60]([CH3:68])[C:49]=1[O:50][CH2:51][C@@H:52]([OH:59])[CH2:53][NH:54][C:55](=[O:58])[CH2:56][OH:57])[CH3:47]>>[CH2:46]([C:48]1[CH:63]=[C:62]([C:64]2[N:67]=[C:37]([C:36]3[CH:40]=[C:41]([CH2:43][CH2:44][CH3:45])[CH:42]=[C:34]([CH:32]=[O:33])[CH:35]=3)[O:39][N:65]=2)[CH:61]=[C:60]([CH3:68])[C:49]=1[O:50][CH2:51][C@@H:52]([OH:59])[CH2:53][NH:54][C:55](=[O:58])[CH2:56][OH:57])[CH3:47]

Participants

4

Reactant 3

HCID 866505083-Formyl-5-propyl-benzoic acidHCID 87208794HCID 87208794, compoundHCID 178436630HCID 178436630, compound

Product 1

HCID 86650517N-((S)-3-{2-ethyl-4-[5-(3-formyl-5-propyl-phenyl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 37.8%

Procedure

The title compound (552 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-propyl-benzoic acid (582 mg, 3.03 mmol) and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (985 mg, 3.03 mmol). LC-MS**: tR=0.78 min; [M+1]+=481.82; 1H NMR (D6-DMSO): δ 0.95 (t, J=7.3 Hz, 3H), 1.23 (t, J=7.5 Hz, 3H), 1.71 (h, J=7.5 Hz, 2H), 2.36 (s, 3H), 2.74 (q, J=7.5 Hz, 2H), 2.82 (t, J=7.5 Hz, 2H), 3.20-3.29 (m, 1H), 3.40-3.48 (m, 1H), 3.71-3.81 (m, 2H), 3.84 (d, J=4.8 Hz, 2H), 3.93-4.01 (m, 1H), 5.31 (d, J=5.0 Hz, 1H), 5.55 (t, J=5.3 Hz, 1H), 7.70 (t, J=5.5 Hz, 1H), 7.82 (s, 2H), 8.07 (s, 1H), 8.33 (s, 1H), 8.52 (s, 1H), 10.15 (s, 1H).

Sources & evidence

ORD record
ord-4d02eb67deee4c7a8c58cdbc519dc15a
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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