Hydrochloric Acid → HCID 11377032, compound

HRID 227335Notes

Reaction equation

HRID 227335 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:40])/[CH:15]=[CH:16]/[C@H:17]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C@@H:18]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1>[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]([OH:40])/[CH:15]=[CH:16]/[C@H:17]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[C@@H:18]([O:24][Si:25]([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:27])[CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11157803HCID 11157803, compound

Product 1

HCID 11377032HCID 11377032, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

(S)-binal-H (0.5 M tetrahydrofuran solution, 335 μL, 0.167 mmol) was added dropwise to a tetrahydrofuran solution (500 μL) of (12S,13S)-(E)-12,13-di-tert-butyldimethylsiloxy-9-oxo-10-octadecaenoic acid t-butyl ester (11) (31.1 mg, 0.0508 mmol) at −78° C. over 5 minutes under the argon atmosphere, and the mixture was stirred at −78° C. for 1 hour. Hydrochloric acid (1.0 N, 1 mL) was added to the reaction solution, the mixture was extracted with chloroform (5 mL) three times, and the organic layer was washed successively with 1.0 N sodium hydroxide (5 mL×3), and saturated brine (5 mL), dried over magnesium sulfate, and concentrated. The resulting colorless oily crude product (32 mg) was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (9S,12S,13S)-(E)-12,13-di-tert-butyldimethylsiloxy-9-hydroxy-10-octadecaenoic acid t-butyl ester (12) as a colorless oily substance (31.0 mg, 99%).

Workup

  1. extractionthe mixture was extracted with chloroform (5 mL) three times
  2. washthe organic layer was washed successively with 1.0 N sodium hydroxide (5 mL×3), and saturated brine (5 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting colorless oily crude product (32 mg) was separated
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a00c1e9dd2eb462e94ceca4111646b23
Source dataset
uspto-grants-2009_07
Patent number
US07560484B2

Reaction notes

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