Dichloromethane → HCID 178421577, compound

HRID 2389088Notes

Reaction equation

HRID 2389088 reaction equation
[CH:1]1([C@H:6]2[CH2:11][CH2:10][C@H:9]([O:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C@:23]3([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]3)[CH:17]=[CH:16]4)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:30]N1C(=O)CCC1=O.C(Cl)Cl>[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[CH:1]1([C@H:6]2[CH2:11][CH2:10][C@H:9]([O:12][C:13]3[C:14]([I:30])=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C@:23]3([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]3)[CH:17]=[CH:16]4)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 178421570HCID 178421570, compound

Product 1

HCID 178421577HCID 178421577, compound

Reagents, catalysts & solvents 1

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

Procedure

The compound was prepared in a manner similar as to that described above using (R)-4-[6-(trans-4-Cyclopentyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (89 mg, 0.00023 mol), N-iodosuccinimide (110 mg, 0.00050 mol), zirconium chloride (0.007 g, 0.00004 mol), and methylene chloride (3 mL, 0.04 mol). ESI-MS: 519 (M+H). 1H NMR (400 MHz, CDCl3) δ=8.17 (d, J=9.0 Hz, 1 H), 7.72-7.59 (m, 2 H), 7.45 (dd, J=1.9, 8.9 Hz, 1 H), 7.24 (d, J=9.0 Hz, 1 H), 5.90 (s, 1 H), 4.44-4.28 (m, 2 H), 4.20 (t, J=4.1 Hz, 1 H), 2.09 (d, J=10.5 Hz, 2 H), 1.91-1.30 (m, 16 H), 1.15-0.87 (m, 5 H)

Workup

  1. customThe compound was prepared in a manner similar as to

Sources & evidence

ORD record
ord-95a9394321a246b98a8a8bedb539f5a4
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

Loading…