Ethanol → HCID 178464707, compound

HRID 2389087Notes

Reaction equation

HRID 2389087 reaction equation
[CH:1]1([C@@H:6]2[CH2:11][CH2:10][C@H:9]([O:12][C:13]3[C:14]([C:30]([F:33])([F:32])[F:31])=[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][C@H:9]3[CH2:10][CH2:11][C@@H:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:7][CH2:8]3)[C:14]=2[C:30]([F:32])([F:33])[F:31])[CH:19]=1)([CH3:29])[CH2:27][OH:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 178421565HCID 178421565, compound

Product 1

HCID 178464707HCID 178464707, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

(R)-4-[6-(cis-4-Cyclopentyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (200 mg, 0.0005 mol) was dissolved in ethanol (2.2 g, 0.049 mol) and treated with 4.2 M lithium hydroxide, monohydrate in water (2.1 mL, 0.0090 mol). The mixture was then heated to 80° C. overnight. The reaction was then cooled to room temperature and diluted with water. Solid formed. Solid was removed via filtration and dried on the filter for 4 hours to give 158 mg the desired product as a white solid (58%). ESI-MS: 419 (M-16)+. 1H NMR (400 MHz, MeOD) δ=8.64-8.50 (m, 1 H), 8.17-7.98 (m, 2 H), 7.98-7.87 (m, 1 H), 7.73-7.62 (m, 1 H), 7.50-7.40 (m, 1 H), 4.21-4.09 (m, 2 H), 3.80-3.58 (m, 2 H), 2.12-1.96 (m, 2 H), 1.85-1.42 (m, 18 H), 1.21-1.05 (m, 2 H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customSolid formed
  3. customSolid was removed via filtration
  4. customdried on the
  5. filtrationfilter for 4 hours

Sources & evidence

ORD record
ord-177f3de80c6044a2ba94c098f2e65d7e
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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