Lithium Hydroxide → HCID 22252997, compound

HRID 1612473Notes

Reaction equation

HRID 1612473 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:16]=[C:15]([N:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[Li+].[OH-]>O1CCOCC1>[CH3:13][N:9]([CH2:10][CH2:11][CH3:12])[C:7](=[O:8])[C:6]1[CH:5]=[C:4]([CH:16]=[C:15]([N:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])[CH:14]=1)[C:3]([OH:23])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68815111HCID 68815111, compound

Product 1

HCID 22252997HCID 22252997, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Methyl-5-(2-oxo-pyrrolidin-1-yl)-N-propyl-isophthalamic acid methyl ester (D64) (0.40 g, 1.25 mmol) in dioxane (15 ml) was treated with 1M LiOH (2.5 ml, 2.5 mmol) and the reaction solution was stirred at room temperature for 2 h. It was then evaporated to dryness and the residue was partitioned between EtOAc and dil. NaHCO3 soln. The aqueous solution was separated and acidified to pH1 with 2M HCl. The product was extracted into EtOAc (×3) and the combined extracts were washed with brine, dried over MgSO4 and evaporated to afford the title compound (D65) (0.30 g, 79%).

Workup

  1. customIt was then evaporated to dryness
  2. customthe residue was partitioned between EtOAc and dil. NaHCO3 soln
  3. customThe aqueous solution was separated
  4. extractionThe product was extracted into EtOAc (×3)
  5. washthe combined extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-b1e5b2c80ef246fda656b5b60b59f7cf
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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