Hydrochloric Acid → HCID 58381697, compound
Reaction equation
OO.O.[OH-].[Li+].[CH2:6]([S:26][C@@H:27]([CH2:43][CH3:44])[C:28](N1[C@@H](C)[C@@H](C2C=CC=CC=2)OC1=O)=[O:29])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25].[O-:45]S([O-])=O.[Na+].[Na+].Cl>O1CCCC1.O>[CH2:6]([S:26][C@@H:27]([CH2:43][CH3:44])[C:28]([OH:29])=[O:45])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
Hydrogen peroxide (30% in water, 0.71 mL, 6.91 mmol) and lithium hydroxide monohydrate (0.15 g, 3.46 mmol) was added to a solution of (4S,5R)-3-((S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoyl)-4-methyl-5-phenyloxazolidin-2-one (0.95 g, 1.73 mmol) in tetrahydrofuran (12 mL) and water (4 mL) held at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 30 minutes. 10% Na2SO3 (aq) (30 mL) was added, the pH was adjusted to ˜2 with 5M HCl and the mixture was extracted twice with heptane (30 mL). The combined organic extract was dried (Na2SO4), filtered and concentrated. The residue was subjected to flash chromatography on silica gel using increasingly polar mixtures of heptane and ethyl acetate (98:8→1:1) as eluent. Concentration of the appropriate fractions afforded 0.15 g (17% yield) of the title product as an oil.
Workup
- customheld at 0° C. under nitrogen
- extractionthe mixture was extracted twice with heptane (30 mL)
- extractionThe combined organic extract
- dry with materialwas dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- temperatureincreasingly polar mixtures of heptane and ethyl acetate (98:8→1:1) as eluent
Sources & evidence
- ORD record
- ord-36a98a011c1f4ea88b60165d71c27c91
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759558B2
Reaction notes
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