Ethanol → HCID 178455815, compound

HRID 2389066Notes

Reaction equation

HRID 2389066 reaction equation
[CH2:1]([C@@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C@:20]2([CH3:26])[CH2:24][O:23]C(=O)[NH:21]2)[CH:14]=[CH:13]3)[CH2:5][CH2:4]1)[CH3:2].C(O)C.O.[OH-].[Li+]>O>[NH2:21][C@@:20]([C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([O:9][C@H:6]3[CH2:5][CH2:4][C@@H:3]([CH2:1][CH3:2])[CH2:8][CH2:7]3)[CH:11]=2)[CH:16]=1)([CH3:26])[CH2:24][OH:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 178455814HCID 178455814, compound

Product 1

HCID 178455815HCID 178455815, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(R)-4-[6-(cis-4-Ethyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.4603 g, 0.001302 mol) was dissolved in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL vial equipped with a magnetic stir bar. 4.2 M Lithium hydroxide, monohydrate in water (2.8 mL) was added and the mixture was heated overnight at 80° C. TLC analysis showed the reaction was complete. The mixture was concentrated to dryness under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated by phase separator cartridge. The organic layer was dried with MgSO4, filtered, concentrated and purified by HPLC to give 0.038 g of the title compound (9% yield). MS: m/z=311.26 [M-NH2]+. 1H NMR (400 MHz, MeOD) δ 0.95 (t, J=7.15 Hz, 3 H), 1.28-1.38 (m, 3 H), 1.39-1.50 (m, 2 H), 1.58-1.74 (m, 4 H), 1.80 (s, 3 H), 2.04-2.14 (m, 2 H), 3.83 (d, J=11.55 Hz, 1 H), 3.94 (d, J=11.55 Hz, 1 H), 4.76 (br. s., 1 H), 7.21-7.30 (m, 2 H), 7.53 (dd, J=8.91, 1.88 Hz, 1 H), 7.82-7.88 (m, 3 H)

Workup

  1. customvial equipped with a magnetic stir bar
  2. concentrationThe mixture was concentrated to dryness under vacuum
  3. additionMethylene chloride (5 mL) and water (5 mL) were added
  4. customthe layers were separated by phase separator cartridge
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-c525f6b34850415796ce9126101b822d
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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