Ethyl Acetate → HCID 178418813, compound

HRID 10564Notes

Reaction equation

HRID 10564 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([O:15]C(=O)C2C=CC(OC)=CC=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(OCC)(=O)C>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([OH:15])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178418876HCID 178418876, compound

Product 1

HCID 178418813HCID 178418813, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Intermediate 118 (32.92 g) in methanol (400 ml) was added with 3 N aqueous sodium hydroxide (163 ml) at room temperature and stirred at 50° C. for 1.5 hours. The reaction mixture was cooled to room temperature, then added with ethyl acetate (400 ml) and washed 4 times with 0.5 N aqueous sodium hydroxide (50 ml each) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (7.94 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed 4 times with 0.5 N aqueous sodium hydroxide (50 ml each)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a30f9f819ce941d6834a0c8a1332c319
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

Loading…