Ethanol → HCID 46196242, compound

HRID 1036425Notes

Reaction equation

HRID 1036425 reaction equation
[CH:1]1([CH:6]2[CH2:11][CH2:10][CH: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(=O)[NH:24]3)[CH:17]=[CH:16]4)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.O.[OH-].[Li+].O>>[NH2:24][C@@:23]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][CH:9]3[CH2:10][CH2:11][CH:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:7][CH2:8]3)[CH:14]=2)[CH:19]=1)([CH3:29])[CH2:27][OH:26]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67413948HCID 67413948, compound

Product 1

HCID 46196242HCID 46196242, compoundYield 90%

Procedure

The compound was prepared in a manner similar as to that described above using (R)-4-[6-(4-Cyclopentyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (200 mg, 0.0005 mol), ethanol (2.2 g, 0.049 mol), 4.2 M lithium hydroxide, monohydrate in water (2.1 mL, 0.0090 mol) to give 114 mg the desired product as a white solid (90%). ESI-MS: 351 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ=7.87 (s, 1H), 7.81-7.55 (m, 3H), 7.31-7.21 (m, 1H), 7.18-7.00 (m, 1H), 4.98-4.59 (m, 3H), 4.43-4.27 (m, 0.63H), 3.57-3.14 (m, 4H), 2.19-0.84 (m, 17H)

Workup

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

Sources & evidence

ORD record
ord-44724b11526848669235ad8d29fd419a
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

Loading…