Ethanol → HCID 46196243, compound

HRID 2389086Notes

Reaction equation

HRID 2389086 reaction equation
[CH:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25]C(=O)[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH2:3][CH3:4])[CH3:2].C(O)C.O.[OH-].[Li+].O>>[NH2:23][C@@:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH:8]3[CH2:7][CH2:6][CH:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH2:10][CH2:9]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67413847HCID 67413847, compound

Product 1

HCID 46196243HCID 46196243, compoundYield 85.5%

Procedure

The compound was prepared in a manner similar as to that described above using (R)-4-[6-(4-sec-Butyl-cyclohexyloxy)-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 152 mg of the desired product as a white solid (50%). ESI-MS: 339 (M-16)+. 1H NMR (400 MHz, DMSO-d6) δ=8.30 (s, 1 H), 7.88 (s, 1 H), 7.75 (d, J=8.8 Hz, 1 H), 7.71-7.56 (m, 1 H), 7.24 (d, J=2.0 Hz, 1 H), 7.12 (dd, J=2.3, 8.8 Hz, 1 H), 4.70 (d, J=5.8 Hz, 1 H), 4.40-4.28 (m, 1 H), 3.55-3.41 (m, 2 H), 2.26-1.07 (m, 12 H), 0.94-0.79 (m, 3 H)

Workup

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

Sources & evidence

ORD record
ord-453a562a7d3b48f0834705f9ced1d020
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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