Ethanol → HCID 46196262, compound

HRID 1036423Notes

Reaction equation

HRID 1036423 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C@:21]2([CH3:27])[CH2:25][O:24]C(=O)[NH:22]2)[CH:15]=[CH:14]3)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(O)C.O.[OH-].[Li+].O>>[NH2:22][C@@:21]([C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([O:10][CH:7]3[CH2:6][CH2:5][CH:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]3)[CH:12]=2)[CH:17]=1)([CH3:27])[CH2:25][OH:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67411654HCID 67411654, compound

Product 1

HCID 46196262HCID 46196262, compoundYield 32.8%

Procedure

The compound was prepared in a manner similar as to that described above using (R)-4-[6-(4-isopropyl-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 56 mg of the desired compound as a yellow brown solid (30%). ESI-MS: 325 (M−16)+. 1H NMR (400 MHz, CDCl3) δ=7.94-7.61 (m, 3H), 7.50 (d, J=8.5 Hz, 1H), 7.23-7.05 (m, 2H), 4.67 (br. s., 1H), 4.33-4.17 (m, 1H), 3.84-3.51 (m, 2H), 2.35-1.75 (m, 4H), 1.68-1.08 (m, 10H), 1.01-0.68 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-c2d64a8607a94794bf0cb3380389c51d
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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