2-Methyl-2-butene → HCID 68840502, compound

HRID 1725341Notes

Reaction equation

HRID 1725341 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:28])[N:7]([CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C@H:14]([OH:27])[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)[CH3:8])([CH3:4])[CH3:3].CN(C1C=CC=CN=1)C.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39].CC=C(C)C>C(Cl)Cl>[CH3:4][C:2]([O:5][C:6](=[O:28])[N:7]([CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][C@@H:14]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[O:27][C:38]1=[O:39])[CH3:8])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 105532-Methyl-2-buteneHCID 218852-DimethylaminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 68841789HCID 68841789, compound

Product 1

HCID 68840502HCID 68840502, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {3-[(R)-2-hydroxy-2-(6-methoxy-quinolin-4-yl)-ethylamino]-propyl}-methyl-carbamic acid dimethyl-ethyl ester (830 mg, 2.1 mmol), 4 (dimethylamino)pyridine (DMAP) (329 mg, 2.66 mmol), 1,1′-carbonyldiimidazole (CDI) (454 mg, 2.77 mmol) and methylene chloride stabilized over amylene (20 ml) was stirred under argon, at room temperature, for 4 days. The solution was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silicagel eluting with methylene chloride-methanol (95-5) to give {3-[(R)-5-(6-methoxy-quinolin-4-yl)-2-oxo-oxazolidin-3-yl]-propyl}-methyl-carbamic acid dimethyl-ethyl ester (770 mg, 88%).

Workup

  1. washThe solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silicagel
  5. washeluting with methylene chloride-methanol (95-5)

Sources & evidence

ORD record
ord-6e940aa32c934b98a34b10890eb67d20
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

Loading…