Citric Acid → HCID 59505190, compound

HRID 1253656Notes

Reaction equation

HRID 1253656 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18]C)=[O:17])[CH:14]=2)[C:9]([CH3:21])([CH3:20])[CH2:8]1)=[O:5].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=2)[C:9]([CH3:21])([CH3:20])[CH2:8]1)=[O:5]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59505444HCID 59505444, compound

Product 1

HCID 59505190HCID 59505190, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 3-(2-chlorobenzamido)-1,1-dimethyl-2,3-dihydro-1H-indene-5-carboxylate (B-39) (120 mg, 0.34 mmol, 1 eq.) was dissolved in a mixture of solvents THF:MeOH:H2O (5:3:1, 5 ml) and LiOH (70 mg, 1.67 mmol, 5 eq.) was added portionwise at 0° C. The reaction mixture was stirred for 4 h and then the solvent was evaporated under reduced pressure. Water (4 ml) was added to the reaction to get a clear solution and it was then acidified with citric acid. This was followed by extraction with EtOAc (2×50 ml). The organic part was washed with brine (20 ml), dried over Na2SO4, filtered and evaporated under reduced pressure to yield the crude product which was purified by column chromatography (silica gel, 5% MeOH/MC) to yield the desired product as a white solid. Yield: 98% (115 mg, 0.34 mmol).

Workup

  1. additionwas added portionwise at 0° C
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater (4 ml) was added to the reaction
  4. customto get a clear solution and it
  5. extractionThis was followed by extraction with EtOAc (2×50 ml)
  6. washThe organic part was washed with brine (20 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto yield the crude product which
  11. customwas purified by column chromatography (silica gel, 5% MeOH/MC)

Sources & evidence

ORD record
ord-5bda4e6c94d54b0a90308722e12f2991
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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