Hydrochloric Acid → HCID 86591007, compound

HRID 227339Notes

Reaction equation

HRID 227339 reaction equation
[C:1]([O:5][C:6](=[O:40])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:39])/[CH:15]=[CH:16]/[C@@H:17]([O:28][Si:29]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[C@@H:18]([O:24][C:25](=[O: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:40])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]([OH:39])/[CH:15]=[CH:16]/[C@@H:17]([O:28][Si:29]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57755999HCID 57755999, compound

Product 1

HCID 86591007HCID 86591007, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

(R)-binal-H (0.5 M tetrahydrofuran solution, 232 μL, 0.116 mmol) was added dropwise to a tetrahydrofuran solution (0.35 mL) of (12R,13S)-(E)-13-acetoxy-9-oxo-12-triisopropylsiloxy-10-octadecaenoic acid t-butyl ester (18) (20.5 mg, 0.0352 mmol) synthesized in Example 4-4) 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, and the mixture was extracted with chloroform (5 mL) three times. The organic layers were combined, washed successively with 1.0 N sodium hydroxide (5 mL×3) and saturated brine (5 mL), dried over sodium sulfate, and concentrated. The resulting colorless oily crude product (21 mg) was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (9R,12R,13S)-(E)-13-acetoxy-9-hydroxy-12-triisopropylsiloxy-10-octadecaenoic acid t-butyl ester (21) (20.3 mg, 99%)

Workup

  1. extractionthe mixture was extracted with chloroform (5 mL) three times
  2. washwashed successively with 1.0 N sodium hydroxide (5 mL×3) and saturated brine (5 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting colorless oily crude product (21 mg) was separated
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-db30a7a684c64fa6a32c776ccc462f12
Source dataset
uspto-grants-2009_07
Patent number
US07560484B2

Reaction notes

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