Hydrochloric Acid → HCID 86706123, compound

HRID 2176278Notes

Reaction equation

HRID 2176278 reaction equation
C([C@H]1COC(=O)N1[C:10](=[O:18])[C@:11]([CH2:15][O:16][CH3:17])([CH3:14])[CH:12]=[CH2:13])(C)C.OO.O.[OH-].[Li+].S(S([O-])=O)([O-])(=O)=[O:25].[Na+].[Na+].Cl>O1CCCC1.O>[CH3:17][O:16][CH2:15][C@:11]([CH3:14])([CH:12]=[CH2:13])[C:10]([OH:18])=[O:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 656671Sodium PyrosulfiteHCID 86706124HCID 86706124, compound

Product 1

HCID 86706123HCID 86706123, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (S)-4-isopropyl-3-((R)-2-methoxymethyl-2-methyl-but-3-enoyl)-oxazolidin-2-one (1.5 g, 5.87 mmol) in tetrahydrofuran (30 mL) and water (15 mL) at 0° C., was added hydrogen peroxide (30% solution, 3 mL, 29.35 mmol) and lithium hydroxide monohydrate (0.59 g, 11.75 mmol). The reaction mixture was stirred at 0° C. for 3 h then was treated with saturated sodium metabisulfite and the pH of the solution was adjusted to 1 with dropwise addition of hydrochloric acid (10 M). The aqueous layer was extracted with ethyl acetate (2×) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated. The crude residue was purified by silica gel chromatography using a Biotage KP-Sil 50 g cartridge, eluting with a gradient of iso-hexanes/ethyl acetate 1:0 to 3:1 to give the title product (0.546 g, 65%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.36 (s, 3H), 3.42 (s, 3H), 3.45 (d, J=8.9 Hz, 1H), 3.62 (d, J=8.9 Hz, 1H), 5.20-5.30 (m, 2H), 6.01 (dd, J=17.6, 10.7 Hz, 1H), 9.80-11.80 (br. s, 1H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customThe crude residue was purified by silica gel chromatography
  7. washeluting with a gradient of iso-hexanes/ethyl acetate 1:0 to 3:1

Sources & evidence

ORD record
ord-7dc2e9da38254641b1febf126f7dac28
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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