Ethanol → HCID 178445754, compound

HRID 1036391Notes

Reaction equation

HRID 1036391 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H: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 178445731HCID 178445731, compound

Product 1

HCID 178445754HCID 178445754, compoundYield 132.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-4-[6-trans-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (Example 24, 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 of 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 48 mg of the title compound (13% yield). MS: m/z=339.47 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.92-0.97 (m, 9H), 1.10-1.20 (m, 1H), 1.23-1.35 (m, 2H), 1.39-1.51 (m, 2H), 1.79 (s, 3H), 1.90-1.98 (m, 2H), 2.29 (dd, J=12.55, 2.01 Hz, 2H), 3.81-3.86 (m, 1H), 3.91-3.96 (m, 1H), 4.32-4.43 (m, 1H), 7.19 (dd, J=8.78, 2.51 Hz, 1H), 7.28 (d, J=2.26 Hz, 1H), 7.53 (dd, J=8.66, 2.13 Hz, 1 H), 7.80-7.89 (m, 3H)

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-d6b9012644a743f188e8b78c95eb3d95
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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