Ethanol → HCID 178444567, compound

HRID 2389058Notes

Reaction equation

HRID 2389058 reaction equation
[CH3:1][C:2]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[C:14]([C:30]([F:33])([F:32])[F:31])=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([C@:23]2([CH3:29])[CH2:27][O:26]C(=O)[NH:24]2)[CH:17]=[CH:16]3)[CH2:8][CH2:7]1)([CH3:5])[CH2:3][CH3:4].O.C(O)C>[OH-].[Li+]>[NH2:24][C@@:23]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][C@H:9]3[CH2:8][CH2:7][C@H:6]([C:2]([CH3:1])([CH3:5])[CH2:3][CH3:4])[CH2:11][CH2:10]3)[C:14]=2[C:30]([F:32])([F:33])[F:31])[CH:19]=1)([CH3:29])[CH2:27][OH:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 178444565HCID 178444565, compound

Product 1

HCID 178444567HCID 178444567, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3939Lithium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (R)-4-{6-[trans-4-(1,1-dimethyl-propyl)-cyclohexyloxy]-5-trifluoromethyl-naphthalen-2-yl}-4-methyl-oxazolidin-2-one (33.00 mg, 0.07119 mmol) in 4.2 M lithium hydroxide in a mixture solvent of water (0.9 mL) and ethanol (0.9 mL) was heated at 80° C. overnight. The solution was concentrated and the residue was partitioned between methylene chloride (4 mL) and water (2 mL). The organic phase was washed with water, dried over MgSO4, filtered and concentrated to give 28 mg of white precipitate, (R)-2-amino-2-{6-[trans-4-(1,1-dimethyl-propyl)-cyclohexyloxy]-5-trifluoromethyl-naphthalen-2-yl}-propan-1-ol (90% yield). MS: m/z=421.30 M-16. 1H NMR (400 MHz, CDCl3) δ ppm 0.74-0.89 (m, 10 H), 1.04-1.22 (m, 2H), 1.22-1.35 (m, 2 H), 1.43-1.61 (m, 5H), 1.82 (d, J=11.29 Hz, 2H), 2.18 (d, J=12.80 Hz, 2H), 2.35 (s, 3H), 3.63-3.82 (m, 2H), 4.23-4.36 (m, 1H), 7.28 (d, 1H), 7.61 (dd, J=9.16, 1.88 Hz, 1H), 7.82-7.95 (m, 2H), 8.19 (d, J=7.78 Hz, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was partitioned between methylene chloride (4 mL) and water (2 mL)
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-87d829f42e664d558a1b66f716d47a77
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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