Ethanol → Trifluoroacetic acid

HRID 2389074Notes

Reaction equation

HRID 2389074 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:29]([F:32])([F:31])[F:30])=[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.[OH2:36].[OH-:37].[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]([F:31])([F:32])[F:30])[CH:18]=1)([CH3:28])[CH2:26][OH:25].[C:13]([OH:37])([C:29]([F:32])([F:31])[F:30])=[O:36]

Participants

6

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 178445733HCID 178445733, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178445757HCID 178445757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(R)-4-[6-(trans4-tert-Butylcyclohexyloxy)-5-trifluoromethylnaphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.3341 g, 0.0007433 mol) was dissolved in ethanol (3.00 mL, 0.0514 mol) in a 40 mL capped vial equipped with a magnetic stir bar. 4.2 M Lithium hydroxide, monohydrate in water (3.00 mL) was added and the mixture was heated at 80° C. overnight. HPLC and LCMS analysis showed that the reaction was complete. The solvent was removed under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated. The combined organic layers were concentrated under vacuum and purified by HPLC to give the title compound as a TFA salt in 0.105 g (33% yield). MS: m/z=407.38 [M-NH2]+. 1H NMR (400 MHz, MeOD) δ 0.93 (s, 9 H), 1.10-1.31 (m, 3 H), 1.58 (d, J=12.55 Hz, 2 H), 1.81 (s, 3 H), 1.89-1.98 (m, 2 H), 2.20-2.29 (m, 2 H), 3.82-3.88 (m, 1 H), 3.92-4.00 (m, 1 H), 4.38-4.48 (m, 1 H), 7.40 (d, J=8.78 Hz, 1 H), 7.64 (dd, J=9.04, 2.01 Hz, 1 H), 7.89 (d, J=2.01 Hz, 1 H), 7.93 (d, J=9.04 Hz, 1 H), 8.21 (d, J=9.04 Hz, 1 H)

Workup

  1. customcapped vial
  2. customequipped with a magnetic stir bar
  3. customThe solvent was removed under vacuum
  4. additionMethylene chloride (5 mL) and water (5 mL) were added
  5. customthe layers were separated
  6. concentrationThe combined organic layers were concentrated under vacuum
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-f1f75320117d42ab9d3915f67e19d29c
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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