Dichloromethane → (R)-4-(6-Hydroxy-5-iodoquinazolin-2-yl)-4-methyloxazolidin-2-one

HRID 709885Notes

Reaction equation

HRID 709885 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[N:6]=[CH:5]2.C(Cl)Cl.[I:22]N1C(=O)CCC1=O>>[OH:1][C:2]1[C:3]([I:22])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[N:6]=[CH:5]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 67408663HCID 67408663, compound

Product 1

HCID 67409863(R)-4-(6-Hydroxy-5-iodoquinazolin-2-yl)-4-methyloxazolidin-2-oneYield 84.1%

Procedure

(R)-4-(6-Hydroxy-quinazolin-2-yl)-4-methyl-oxazolidin-2-one (330.0 mg, 0.001346 mol) was dissolved in methylene chloride (500 mL, 8 mol), (heterogeneous) followed by N-iodosuccinimide (302.8 mg, 0.001346 mol) at 23° C. The reaction mixture was then sonicated for 30 seconds, and all the solvent was removed under vacuum (rotavap). The residue was purified via chromatography (SiO2, 20 gm, 0-100% ethyl acetate/hexanes) to give 420 mg of desired product (84%). 1H NMR (MeOD) δ: 9.50 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H), 4.99 (d, J=8.8 Hz, 1H), 4.48 (d, J=8.8 Hz, 1H), 1.79 (s, 3H). MS (M+1): 372.00.

Workup

  1. customThe reaction mixture was then sonicated for 30 seconds
  2. customall the solvent was removed under vacuum (rotavap)
  3. customThe residue was purified via chromatography (SiO2, 20 gm, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0db87ec229c2412db8be72ba5cadfc91
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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