Sodium Chlorite → 3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-5-methoxy-benzoic acid
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:8][C:9]1[CH:14]=[C:13]([C:15](=[O:23])NC2CCNCC2)[CH:12]=[C:11]([O:24][CH3:25])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C([O:29]C(=O)C(OC1C=C(OC)C=C(C=O)C=1)(C)C)C.Cl([O-])=O.[Na+]>>[CH2:1]([O:3][C:4]([C:5]([CH3:6])([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([O:24][CH3:25])[CH:10]=1)[C:15]([OH:23])=[O:29])[CH3:7])=[O:26])[CH3:2]Participants
Procedure
In analogy to the procedure described in example 50k), 2-[3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-2-methyl-propionic acid ethyl ester [prepared by i) oxidation of 2-(3-formyl-5-methoxy-phenoxy)-2-methyl-propionic acid ethyl ester with sodium chlorite in analogy to example 60c) to give 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-5-methoxy-benzoic acid; ii) subsequent condensation with 4-amino-piperidine-carboxylic acid tert-butyl ester, using acid activation with 2-chloro-4,6-dimethoxy-1,3,5-triazine in analogy to the procedure described in example 50 h) followed by Boc cleavage with TFA in analogy to the procedure described in example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless foam. MS: 561.6 (MH+).
Sources & evidence
- ORD record
- ord-27562bb5f4484948bd822a385e59d1f6
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772253B2
Reaction notes
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