Methanol → {3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid methyl ester

HRID 600273Notes

Reaction equation

HRID 600273 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][N:10]=2)=[CH:4][C:3]=1[N:20]1[C:24](=[O:25])[CH:23]([CH3:26])[N:22]([CH2:27][C:28]([OH:30])=[O:29])[C:21]1=[O:31].S(=O)(=O)(O)O.[CH3:37]O>>[CH3:37][O:29][C:28](=[O:30])[CH2:27][N:22]1[CH:23]([CH3:26])[C:24](=[O:25])[N:20]([C:3]2[CH:4]=[C:5]([CH2:8][C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](=[O:19])[NH:11][N:10]=3)[CH:6]=[CH:7][C:2]=2[F:1])[C:21]1=[O:31]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59856564{3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid

Product 1

HCID 59856567{3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid methyl ester

Conditions

Temperature
70 °C

Procedure

To a solution of {3-[2-fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid (36A)(0.04 g, 0.094 mmol) in methanol (4 ml) was added concentrated sulfuric acid (1 ml) and stirred at 70° C. for 90 minutes before being cooled to room temperature. The reaction mixture was then concentrated in vacuo, diluted with water (10 ml) an extracted with ethyl acetate (2×10 ml). The organic layer was then dried over sodium sulfate and concentrated in vacuo to afford a colourless oil. Single peak in LC-MS, (52 mg, 95% purity) and required no further purification; m/z (LC-MS, ESP), RT=3.24 mins (M+H) 439;

Workup

  1. temperaturebefore being cooled to room temperature
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additiondiluted with water (10 ml)
  4. extractionan extracted with ethyl acetate (2×10 ml)
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford a colourless oil
  8. customno further purification

Sources & evidence

ORD record
ord-1ae03753d14049c2b8185948c5b0149c
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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