Ethanol → HCID 178445754, compound

HRID 1036412Notes

Reaction equation

HRID 1036412 reaction equation
[C: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)([CH3:4])([CH3:3])[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][C@H:8]3[CH2:7][CH2:6][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH2:9]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 67414115(R)-4-[6-(4-tert-Butylcyclohexyloxy)naphthalen-2-yl]-4-methyl-oxazolidin-2-one

Product 1

HCID 178445754HCID 178445754, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-4-[6-(4-tert-Butylcyclohexyloxy)naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.03878 g, 0.0001016 mol) was dissolved in ethanol (1.00 mL, 0.0171 mol) in a capped 40 mL vial equipped with a magnetic stir bar. 4.2 M Lithium hydroxide, monohydrate in water (1.00 mL) was added and the reaction was refluxed overnight. TLC analysis showed that the reaction was complete. The solvent was removed under vacuum. The product was diluted in methylene chloride (5 mL) and water was added (5 mL). The layers were separated and the organic phase was then concentrated to dryness under vacuum, and purified by HPLC to give 0.0048 g of the title compound (13% yield). MS: m/z=339.47 [M−NH2]+

Workup

  1. customvial equipped with a magnetic stir bar
  2. temperaturethe reaction was refluxed overnight
  3. customThe solvent was removed under vacuum
  4. additionThe product was diluted in methylene chloride (5 mL)
  5. additionwater was added (5 mL)
  6. customThe layers were separated
  7. concentrationthe organic phase was then concentrated to dryness under vacuum
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-e96879da67964403bc18b59d98724cb3
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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