Triacetoxyperiodinane → 2-(4-Chloro-2,6-dimethyl-phenoxy)-4-(1-ethyl-2-oxo-propylamino)-6-methyl-nicotinic acid methyl ester

HRID 1245708Notes

Reaction equation

HRID 1245708 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25](=[O:50])[C:26]1[C:31]([NH:32][CH:33]([CH2:37][CH3:38])[CH:34]([OH:36])[CH3:35])=[CH:30][C:29]([CH3:39])=[N:28][C:27]=1[O:40][C:41]1[C:46]([CH3:47])=[CH:45][C:44]([Cl:48])=[CH:43][C:42]=1[CH3:49]>>[CH3:23][O:24][C:25](=[O:50])[C:26]1[C:31]([NH:32][CH:33]([CH2:37][CH3:38])[C:34](=[O:36])[CH3:35])=[CH:30][C:29]([CH3:39])=[N:28][C:27]=1[O:40][C:41]1[C:46]([CH3:47])=[CH:45][C:44]([Cl:48])=[CH:43][C:42]=1[CH3:49]

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 695877062-(4-Chloro-2,6-dimethyl-phenoxy)-4-(1-ethyl-2-hydroxy-propylamino)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 695875392-(4-Chloro-2,6-dimethyl-phenoxy)-4-(1-ethyl-2-oxo-propylamino)-6-methyl-nicotinic acid methyl ester

Procedure

The title compound was prepared by Dess-Martin oxidation of 2-(4-chloro-2,6-dimethyl-phenoxy)-4-(1-ethyl-2-hydroxy-propylamino)-6-methyl-nicotinic acid methyl ester. A white solid was obtained after silica gel column chromatography. 1H NMR(CDCl3) d 8.6(d,1H), 7.01(s,2H), 5.899s,1H), 3.9–4.0(m,1H), 3.90(s,3H), 2.17(s,3H), 2.07(s,3H), 2.05(s,3H), 1.859m,1H), 1.93(m,1H), 1.00(t,3H) ppm.

Workup

  1. customA white solid was obtained after silica gel column chromatography

Sources & evidence

ORD record
ord-e113b06edcef4453abba3d235ced93e7
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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