Hydrochloric Acid → HCID 16732377, compound

HRID 1363829Notes

Reaction equation

HRID 1363829 reaction equation
[Si:1]([O:8][C@H:9]([CH2:15][CH2:16][C@:17]1([CH3:30])[C@H:21]([CH:22]=[CH2:23])[O:20][C@H:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:18]1)[CH2:10][C:11]([O:13]C)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1.CO.O>[Si:1]([O:8][C@H:9]([CH2:15][CH2:16][C@:17]1([CH3:30])[C@H:21]([CH:22]=[CH2:23])[O:20][C@H:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:18]1)[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59516414HCID 59516414, compound

Product 1

HCID 16732377HCID 16732377, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(2S,4R,5S)-4-methyl-2-phenyl-5-vinyl-1,3-dioxolan-4-yl]pentanoate (14.6 g, 33.6 mmol) was dissolved in a mixed solution of THF (140 ml)-methanol (140 ml)-water (70.0 ml) and anhydrous lithium hydroxide (4.02 g, 168 mmol) was added. The reaction solution was stirred at room temperature for four and a half hours. The reaction solution was poured into 0.5N hydrochloric acid, which was then extracted with ethyl acetate. After the organic layer was washed with water and brine sequentially, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1→2:1) to obtain the title compound (14.1 g) as a colorless oil.

Workup

  1. additionwas added
  2. extractionwas then extracted with ethyl acetate
  3. washAfter the organic layer was washed with water and brine sequentially
  4. dry with materialit was dried over anhydrous magnesium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-1dfe8f1e1e6c492f8b8572d4881764d5
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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