Ethanol → HCID 178445751, compound

HRID 1036484Notes

Reaction equation

HRID 1036484 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[C:13]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=3)=[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)[C:13]=2[C:29]2[CH:30]=[CH:31][C:32]([O:35][C:36]([F:38])([F:39])[F:37])=[CH:33][CH:34]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67412138(R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(trifluoromethoxy)phenyl)naphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 178445751HCID 178445751, compoundYield 69%

Conditions

Temperature
80 °C

Procedure

(R)-4-[6-(4-tert-Butyl-cyclohexyloxy)-5-(4-trifluoromethoxy-phenyl)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.2041 g, 0.0003768 mol) was dissolved in ethanol (4.00 mL, 0.0685 mol) in a capped 40 mL EPA vial equipped with a magnetic stir bar. 4.2 M lithium hydroxide, monohydrate in water (2.00 mL, 0.00840 mol) was added and the mixture was stirred overnight at 80° C. HPLC analysis showed that the reaction was complete. The reaction mixture was concentrated to dryness under reduced pressure. The product was partitioned between water and methylene chloride. The combined organic phase was dried over MgSO4, filtered, concentrated and purified by flash chromatography [0-50% of 2M NH3 solution in MeOH (10% in methylene chloride) and methylene chloride to give the title compound in 69% yield. MS: m/z=499.23 [M−NH2]+. 1H NMR (MeOD) δ: 7.93-7.96 (m, 1H), 7.91 (d, J=9.3 Hz, 1H), 7.47-7.52 (m, 1H), 7.38-7.45 (m, 6H), 4.06-4.16 (m, 1H), 3.72 (d, J=10.8 Hz, 1H), 3.67 (d, J=10.8 Hz, 1H), 1.99-2.07 (m, 2H), 1.76-1.84 (m, 2H), 1.51 (s, 3H), 0.91-1.24 (m, 5H), 0.86 (s, 9H)

Workup

  1. customvial equipped with a magnetic stir bar
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. customThe product was partitioned between water and methylene chloride
  4. dry with materialThe combined organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography [0-50% of 2M NH3 solution in MeOH (10% in methylene chloride) and methylene chloride

Sources & evidence

ORD record
ord-5a4d32d8cb5a4e1985b8b4e64207e082
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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