Hydrochloric Acid → HCID 22251491, compound

HRID 916503Notes

Reaction equation

HRID 916503 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-259f02c2f97741e288b7997b73e3f2d0
Source dataset
uspto-grants-2007_09
Patent number
USRE039850E1

Reaction notes

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