L-Methioninol → 2-(4-Chloro-2,6-dimethyl-phenoxy)-4-(1-hydroxymethyl-3-methylsulfanyl-propylamino)-6-methyl-nicotinic acid methyl ester

HRID 2308001Notes

Reaction equation

HRID 2308001 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=1[CH3:21].[NH2:23][C@H:24]([CH2:29][OH:30])[CH2:25][CH2:26][S:27][CH3:28]>>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([NH:23][CH:24]([CH2:29][OH:30])[CH2:25][CH2:26][S:27][CH3:28])=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=1[CH3:21]

Participants

3

Reactant 2

HCID 2724404L-MethioninolHCID 248062602-(4-Chloro-2,6-dimethyl-phenoxy)-4-chloro-6-methyl-nicotinic acid methyl ester

Product 1

HCID 695879002-(4-Chloro-2,6-dimethyl-phenoxy)-4-(1-hydroxymethyl-3-methylsulfanyl-propylamino)-6-methyl-nicotinic acid methyl ester

Conditions

Temperature
134 °C

Procedure

A mixture of 2-(4-chloro-2,6-dimethyl-phenoxy)-4-chloro-6-methyl-nicotinic acid methyl ester and L-methioninol in N-methyl-2-pyrodone (NMP) was heated in a 134° C. oil bath for 3 hr. Standard work-up procedure and purification provided the title compound. 1H NMR(CDCl3) d 8.25(d,1H), 7.02(s,2H), 6.30(s,1H), 3.85(s,3H), 3.6-3.9(m,3H), 2.5-2.7(m,2H), 2.14(s,3H), 2.10(s,3H), 2.06(s,6H), 1.8-2.1 (m,2H)ppm.

Workup

  1. customStandard work-up procedure and purification

Sources & evidence

ORD record
ord-0fd7e410e2a14b64b5402202c5282bb3
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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