Hydrochloric Acid → HCID 22251491, compound

HRID 2402418Notes

Reaction equation

HRID 2402418 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl>O.C1COCC1>[O:19]=[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18618679HCID 18618679, compound

Product 1

HCID 22251491HCID 22251491, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl ester 47 (195 mg, 0.73 mmol) in water/THF (1:1, 0.07M) was added LiOH (46 mg, 1.1 mmol). The resulting solution was stirred overnight at room temperature or until no starting material was detected by TLC. HCl 1N was added and the solution was extracted with EtOAc and the organic layer was dried over anhydrous MgSO4. Filtration and evaporation of the solvent under vacuum followed by purification by column chromatography using 10% MeOH/CH2Cl2, gave the title compound.

Workup

  1. extractionthe solution was extracted with EtOAc
  2. dry with materialthe organic layer was dried over anhydrous MgSO4
  3. filtrationFiltration and evaporation of the solvent under vacuum
  4. customfollowed by purification by column chromatography

Sources & evidence

ORD record
ord-6834da6ae8494e58aad8dd3471390423
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

Loading…