3-Ethyl-4-formyl-benzoic acid → HCID 86650514, compound

HRID 1958816Notes

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.[CH2:32]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[CH:43]=[O:44])[C:37]([OH:39])=O)[CH3:33].[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]([CH:43]=[O:44])=[C:34]([CH2:32][CH3:33])[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

Reactant 3

HCID 866505103-Ethyl-4-formyl-benzoic acid

HCID 87208794HCID 87208794, compound

HCID 178436630HCID 178436630, compound

Product 1

HCID 86650514HCID 86650514, compoundYield 49.8%

Procedure

The title compound (183 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-ethyl-4-formyl-benzoic acid (140 mg, 0.786 mmol) and N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (256 mg, 0.786 mmol). LC-MS**: tR=0.72 min; [M+1]+=468.25; 1H NMR (D6-DMSO): δ 1.23 (t, J=7.8 Hz, 3H), 1.28 (t, J=7.3 Hz, 3H), 2.36 (s, 3H), 2.70-2.78 (m, 3H), 3.19 (q, J=7.3 Hz, 2H), 3.23-3.29 (m, 1H), 3.40-3.48 (m, 1H), 3.71-3.81 (m, 2H), 3.84 (d, J=5.5 Hz, 2H), 3.94-4.00 (m, 1H), 5.31 (d, J=5.3 Hz, 1H), 5.56 (t, J=5.5 Hz, 1H), 7.71 (t, J=5.8 Hz, 1H), 7.82 (s, 2H), 8.09 (d, J=8.0 Hz, 1H), 8.19-8.24 (m, 2H), 10.38 (s, 1H).

Sources & evidence

ORD record: ord-3d0d67c227d64fae9f36a968bdb7652c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

Loading…