Ethanol → HCID 178464725, compound

HRID 1036515Notes

Reaction equation

HRID 1036515 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-9337fd2feea047c6ac2bfe6f13475598
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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