Trifluoromethanesulfonic acid, lithium salt → 3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-2-hydroxypropionic acid methyl ester

HRID 723914Notes

Reaction equation

HRID 723914 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH3:13])[C:7](=[O:14])[CH2:6][CH2:5]2.[CH3:15][O:16][C:17]([C@@H:19]1[O:21][CH2:20]1)=[O:18].FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C>[CH3:15][O:16][C:17](=[O:18])[CH:19]([OH:21])[CH2:20][NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH3:13])[C:7](=[O:14])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 9877347Methyl (2R)-2-oxiranecarboxylateHCID 218777156-amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 684917263-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-2-hydroxypropionic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one (Step 3, 2.25 g, 0.0116 mol), methyl (2R)-glycidate (1.18 g, 0.0116 mol) and lithium trifluoromethanesulfonate (1.81 g, 0.0116 mol) in acetonitrile (10 ml) are heated at 90° C. overnight. The reaction is concentrated and the residue diluted with ethyl acetate, washed with water and saline, dried (MgSO4) and evaporated. The residue is purified by flash column chromatography (50% ethyl acetate/hexane) to give the title compound as a yellow solid (2.13 g, 62%); MS (m/z): [M+H]+=297.

Workup

  1. concentrationThe reaction is concentrated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with water and saline
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3ef6839eecad474f8a4d155e2ab712ff
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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