Dichloromethane → HCID 67411503, compound

HRID 2389099Notes

Reaction equation

HRID 2389099 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.[I:19]N1C(=O)CCC1=O.C(Cl)Cl>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[OH:1][C:2]1[C:3]([I:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67411503HCID 67411503, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-Catalyst

Procedure

The mixture of (R)-4-(6-Hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (221.7 mg, 0.0009114 mol), N-iodosuccinimide (226 mg, 0.00100 mol) and zirconium tetrachloride (33 mg, 0.00014 mol) in methylene chloride (16 mL, 0.25 mol) was stirred at room temperature for 3 h. After filtrating through Celite and washing with methylene chloride, the concentrated residue was chromatographed to give (R)-4-(6-hydroxy-5-iodonaphthalen-2-yl)-4-methyloxazolidin-2-one as a light yellow solid (290 mg, 86%). LCMS: Rf=1.33 min (370.07, M+1, 100%), 1H NMR (400 MHz, MeOD) δ=8.10 (d, J=8.9 Hz, 1 H), 7.79 (s, 1 H), 7.77 (d, J=8.8 Hz, 1 H), 7.56 (dd, J=2.1, 8.9 Hz, 1 H), 7.18 (d, J=8.8 Hz, 1 H), 4.52 (d, J=8.5 Hz, 1 H), 4.43 (d, J=8.5 Hz, 1 H), 1.80 (s, 3 H).

Workup

  1. filtrationAfter filtrating through Celite
  2. washwashing with methylene chloride
  3. customthe concentrated residue was chromatographed

Sources & evidence

ORD record
ord-77785dae5ad14da8a0002d2cdd673377
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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