Hydrochloric Acid → HCID 57756001, compound

HRID 227338Notes

Reaction equation

HRID 227338 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 57756001HCID 57756001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

(S)-binal-H (0.5 M tetrahydrofuran solution, 215 μl, 0.107 mmol) was added dropwise to a tetrahydrofuran solution (300 μl) of (12R,13S)-(E)-13-acetoxy-9-oxo-12-triisopropylsiloxy 10-octadecaenoic acid t-butyl ester (18) (18.7 mg, 0.033 mmol) at −78° C. over 5 minutes under the argon atmosphere, and the mixture was stirred at −78° C. for 1 hour and 30 minutes. 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 layer was washed successively with 1.0 N sodium hydroxide (5 mL) and saturated brine (5 mL), dried over sodium sulfate, and concentrated. The resulting colorless oily crude product (20 mg) was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (9S,12R,13S)-(E)-13-acetoxy-9-hydroxy-12-triisopropylsiloxy-10-octadecaenoic acid t-butyl ester (19) as a colorless oily substance (18.6 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) and saturated brine (5 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting colorless oily crude product (20 mg) was separated
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a74eae9742644c88b9b6f62f1bcf5856
Source dataset
uspto-grants-2009_07
Patent number
US07560484B2

Reaction notes

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