AcOH THF water → HCID 11268538, compound

HRID 1888301Notes

Reaction equation

HRID 1888301 reaction equation
[CH3:1][C@@H:2]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3][C@H:4]([O:22]C1CCCCO1)/[CH:5]=[CH:6]/[C@H:7]1[CH2:11][CH2:10][C:9](=[O:12])[C@@H:8]1[CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20].C(O)(=O)C.O1CCCC1.O>C(OCC)(=O)C>[OH:22][C@@H:4]([CH2:3][C@@H:2]([CH3:1])[CH2:29][CH2:30][CH2:31][CH3:32])/[CH:5]=[CH:6]/[C@H:7]1[CH2:11][CH2:10][C:9](=[O:12])[C@@H:8]1[CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 21877175AcOH THF waterHCID 66859767HCID 66859767, compound

Product 1

HCID 11268538HCID 11268538, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To the compound 23 (171 mg) was added acetic acid/tetrahydrofuran/water (65:10:35) (4.00 mL) and the solution was stirred at 50° C. for 50 minutes. The reaction solution was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1), to give the title compound (119 mg) having the following physical data.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ee52cc8ee9c94b7ca3d59f4a6afc66ee
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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