Ethanol → HCID 178445758, compound

HRID 2389049Notes

Reaction equation

HRID 2389049 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[C:12]([O:13][C@H:14]2[CH2:19][CH2:18][C@@H:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:15]2)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C@:24]1([CH3:30])[CH2:28][O:27]C(=O)[NH:25]1)=[CH:8]2.[OH-].[Li+].C(O)C.O>>[NH2:25][C@@:24]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:12]([O:13][C@H:14]3[CH2:15][CH2:16][C@@H:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19]3)[C:3]=2[C:2]([F:31])([F:32])[F:1])[CH:8]=1)([CH3:30])[CH2:28][OH:27]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178445734HCID 178445734, compound

Product 1

HCID 178445758HCID 178445758, compoundYield 99.2%

Procedure

The mixture of (R)-4-(5-trifluoromethyl-6-(cis-4-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (324.6 mg, 0.0007221 mol) and lithium hydroxide (190 mg, 0.0079 mol) in ethanol (10 mL, 0.2 mol) and water (3 mL, 0.1 mol) was heated to reflux for overnight. LCMS showed reaction completed. The solvent was removed under vacuum and the residue was partitioned between water and CH2Cl2. The aqueous layer was extensively extracted with CH2Cl2. And the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into DCM and subjected to chromatographic purification with CH2Cl2/MeOH (10:90 to 80:20) to give the product (303.5 mg, 99% yield). LCMS 407.28 ([M-NH2]+, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.92 (t, J=6.8 Hz, 3H), 1.20-1.69 (m, 13H), 1.51 (s, 3H), 2.05 (dd, J=13.2, 2.3 Hz, 2 H), 3.66 (d, J=10.9 Hz, 1H), 3.73 (d, J=10.9 Hz, 1H), 4.83 (brs, 1H), 7.43 (d, J=9.4 Hz, 1H), 7.68 (dd, J=9.4, 2.3 Hz, 1H), 7.92 (d, J=2.3 Hz, 1H), 8.03 (d, J=9.4 Hz, 1H), 8.12 (dd, J=9.0, 1.8 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. customreaction
  4. customThe solvent was removed under vacuum
  5. customthe residue was partitioned between water and CH2Cl2
  6. extractionThe aqueous layer was extensively extracted with CH2Cl2
  7. dry with materialAnd the combined organic phase was dried over Na2SO4
  8. customsubjected to chromatographic purification with CH2Cl2/MeOH (10:90 to 80:20)

Sources & evidence

ORD record
ord-8fc51c63013b4b8ab6dbe9b1a8775aa6
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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