Phosgene → (5R)-3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester

HRID 896191Notes

Reaction equation

HRID 896191 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7](=[O:25])[CH:8]([OH:24])[CH2:9][NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([F:21])[CH:20]=1)[N:17]([CH3:22])[C:16](=[O:23])[CH2:15][CH2:14]2.C(N(CC)CC)C>ClCCl>[CH3:5][O:6][C:7]([C@@H:8]1[O:24][C:1](=[O:2])[N:10]([C:11]2[CH:12]=[C:13]3[C:18](=[C:19]([F:21])[CH:20]=2)[N:17]([CH3:22])[C:16](=[O:23])[CH2:15][CH2:14]3)[CH2:9]1)=[O:25]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 684917263-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-2-hydroxypropionic acid methyl ester

Product 1

HCID 68491736(5R)-3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosgene (20% solution in toluene, 4.07 ml, 7.69 mmol) is added dropwise at 0° C. to 3-(8-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-2-hydroxypropionic acid methyl ester (Step 4, 1.81 g, 6.41 mmol) and triethylamine (2.23 ml, 16.0 mmol) in dichloromethane (25 ml). The mixture is allowed to warm. to room temperature and stirred for an additional hour. The reaction is washed with 2N aqueous hydrochloric acid 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 white solid (1.71 g, 83%); MS (m/z): [M+H]+=323.

Workup

  1. temperatureto warm
  2. washThe reaction is washed with 2N aqueous hydrochloric acid and saline
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue is purified by flash column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4abbe8055da24874b29e86d18237d01a
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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