Ethanol → HCID 46196356, compound

HRID 1036461Notes

Reaction equation

HRID 1036461 reaction equation
[CH:1]([O:4][C:5]1[CH:28]=[CH:27][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C@:20]2([CH3:26])[CH2:24][O:23]C(=O)[NH:21]2)[CH:14]=[CH:13]3)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(O)C.[OH-].[Li+].O>>[NH2:21][C@@:20]([C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([O:9][C:8]3[CH:27]=[CH:28][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=3)[CH:11]=2)[CH:16]=1)([CH3:26])[CH2:24][OH:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67414948HCID 67414948, compound

Product 1

HCID 46196356HCID 46196356, compound

Conditions

Temperature
80 °C

Procedure

(R)-4-[6-(4-isopropoxy-phenoxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (1.092 g, 0.002894 mol) was dissolved in ethanol (60 mL, 1 mol), followed by 4 M lithium hydroxide in water (30 mL, 0.1 mol). The reaction mixture was then heated at 80° C. for 5 hours. LCMS indicates no SM remains with mostly DP RT=1.26 min, M+1=352. All solvent was removed under reduced pressure. The solid was triturated with DCM, and the solvent was then washed with water. Organic was dried over MgSO4, filtered and concentrated to dryness. Residue was then placed on the high vac for 5 hours. 1H NMR and LCMS were consistent with structure. ESI-MS: 360 (M−16)+ 1H NMR (400 MHz, CHLOROFORM-d) δ=7.88-7.67 (m, 3H), 7.50-7.21 (m, 5H), 7.00 (m, 2H), 6.45-6.13 (m, 1H), 4.82-4.67 (m, 1H), 4.43 (s, 2H), 2.17 (s, 3H), 1.46-1.28 (d, J=9.0 Hz, 6H)

Workup

  1. customAll solvent was removed under reduced pressure
  2. customThe solid was triturated with DCM
  3. washthe solvent was then washed with water
  4. dry with materialOrganic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-db861e4e83c944f7a9584631d43cc351
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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