Hydrochloric Acid → HCID 16732377, compound

HRID 1160568Notes

Reaction equation

HRID 1160568 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-00b88d407674472c969f7fbfc18a6b57
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

Loading…