Ethanol → HCID 46196230, compound

HRID 2389081Notes

Reaction equation

HRID 2389081 reaction equation
[CH:1]1([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([C@:18]2([CH3:24])[CH2:22][O:21]C(=O)[NH:19]2)[CH:12]=[CH:11]3)[CH2:3][CH2:2]1.C(O)C.O.[OH-].[Li+].O>>[NH2:19][C@@:18]([C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:7][CH:4]3[CH2:5][CH2:6][CH:1]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:2][CH2:3]3)[CH:9]=2)[CH:14]=1)([CH3:24])[CH2:22][OH:21]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67413795HCID 67413795, compound

Product 1

HCID 46196230HCID 46196230, compoundYield 46%

Procedure

The compound was prepared in a manner similar as to that described above using (R)-4-[6-(Bicyclohexyl-4-yloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (200 mg, 0.0005 mol), ethanol (2.2 g, 0.049 mol), and 4.2 M lithium hydroxide, monohydrate in water (2.1 mL, 0.0090 mol) to give 46 mg of the desired product as a white solid (46%). ESI-MS: 365 (M-16)+. 1H NMR (400 MHz, CDCl3) δ=7.99-7.55 (m, 3 H), 7.29-7.12 (m, 1 H), 7.08 (s, 2 H), 4.70 (s, 1 H), 4.32-4.17 (m, 1 H), 3.27-2.99 (m, 2 H), 2.32-0.81 (m, 25 H).

Workup

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

Sources & evidence

ORD record
ord-8d8b618930b9488ea83cb0e42682de65
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

Loading…