Ethanol → HCID 178464725, compound

HRID 2389175Notes

Reaction equation

HRID 2389175 reaction equation
[CH3:1][C@@:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]4[CH2:24][CH2:23][C@@H:22]([C:25]([F:28])([F:27])[F:26])[CH2:21][CH2:20]4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.[OH-].[Li+].C(O)C>>[NH2:3][C@@:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]3[CH2:24][CH2:23][C@@H:22]([C:25]([F:26])([F:27])[F:28])[CH2:21][CH2:20]3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 178421575HCID 178421575, compound

Product 1

HCID 178464725HCID 178464725, compound

Procedure

The mixture of (R)-4-Methyl-4-[6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one (30.6 mg, 0.0000778 mol) and 4.20 M aqueous lithium hydroxide (0.300 mL, 0.00126 mol) and ethanol (0.900 mL, 0.0154 mol) was heated to reflux for 4.5 h. The reaction was evaporated to remove organics. The aqueous phase was extracted with methylene chloride, and the organics were evaporated. The residue was purified by silica gel chromatography using 0-100% methanol in methylene chloride to yield the product in 13.4 mg yield (47%). MS: m/z=351.20 [M-NH2]+. 1H NMR (400 MHz, METHANOL-d4) δ ppm: 7.87 (d, J=2.0 Hz, 1H), 7.80 (d, J=9.0 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.57 (dd, J=8.5, 2.0 Hz, 1H), 7.25 (d, J=2.3 Hz, 1H), 7.18 (dd, J=8.8, 2.5 Hz, 1H), 4.77-4.82 (m, 1H), 3.74 (d, J=10.8 Hz, 1H), 3.70 (d, J=10.8 Hz, 1H), 2.25-2.34 (m, 1H), 2.18-2.25 (m, 2H), 1.65-1.88 (m, 6H), 1.54 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. customThe reaction was evaporated
  4. customto remove organics
  5. extractionThe aqueous phase was extracted with methylene chloride
  6. customthe organics were evaporated
  7. customThe residue was purified by silica gel chromatography
  8. customto yield the product in 13.4 mg
  9. customyield (47%)

Sources & evidence

ORD record
ord-ffc1cd57394a4b769553283b1c47b54b
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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