Sodium Hydroxide → 4-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1H-pyrrole-2-carboxylic acid

HRID 1025568Notes

Reaction equation

HRID 1025568 reaction equation
C[O:2][C:3]([C:5]1[N:6](C(OC(C)(C)C)=O)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[N:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=4)[C:17]3=[O:30])[C:11]=2[CH2:31][O:32]C(=O)C)[CH:9]=1)=[O:4].[OH-].[Na+]>O1CCOCC1.O>[C:26]([C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:30])[N:16]([C:12]1[C:11]([CH2:31][OH:32])=[C:10]([C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[NH:6][CH:7]=3)[CH:15]=[CH:14][CH:13]=1)[N:25]=[CH:24]2)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 710081234-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 710084124-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1H-pyrrole-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (136 mg, 0.24 mmol) in 5 mL of dioxane and 5 mL of water was added NaOH (40 mg) and the reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated under reduced pressure. The residue was dissolved in 8 mL of water, and acidified with 1 N HCl to pH 3-4. The mixture was extracted with ethyl acetate (5 mL×3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give 4-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1H-pyrrole-2-carboxylic acid (99 mg, yield 100%). LC-MS calcd for C24H23N3O4 (m/e) 417.17, obsd 418 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 8 mL of water
  3. extractionThe mixture was extracted with ethyl acetate (5 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e170261fed464c1ead4ad07fc2d8ab3a
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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