Hexane → Methyl 2-(2-tert-butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

HRID 2066586Notes

Reaction equation

HRID 2066586 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:17](=[O:18])[C:16]([OH:19])=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=3)[C:14]2=[O:20])=[C:9]1[C:30]([O:32][CH3:33])=[O:31])([CH3:4])([CH3:3])[CH3:2].[CH3:35][Si](C=[N+]=[N-])(C)C.CCCCCC>ClCCl.CO>[C:1]([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:17](=[O:18])[C:16]([O:19][CH3:35])=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=3)[C:14]2=[O:20])=[C:9]1[C:30]([O:32][CH3:33])=[O:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 66997817Methyl 2-(2-tert-butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 66996943Methyl 2-(2-tert-butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of methyl 2-(2-tert-butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (0.70 g, 1.41 mmol) and a solution of trimethylsilyldiazomethane in hexane (1.0 mL, 2.0 mmol; 2M) in dichloromethane-methanol (4 & 2 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. The residue was subject to column chromatography on silica gel euting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions provided the title compound. ES MS M+1=509

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-4454d8bcded44820886d94092c3c3356
Source dataset
uspto-grants-2012_10
Patent number
US08293731B2

Reaction notes

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