Methanol → HCID 59856552, compound

HRID 600275Notes

Reaction equation

HRID 600275 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])[C:23]([CH3:27])([CH3:26])[N:22]([CH2:28][C:29]([OH:31])=[O:30])[C:21]1=[O:32].S(=O)(=O)(O)O.[CH3:38]O>>[CH3:38][O:30][C:29](=[O:31])[CH2:28][N:22]1[C:23]([CH3:26])([CH3:27])[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:32]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59856551HCID 59856551, compound

Product 1

HCID 59856552HCID 59856552, compound

Conditions

Temperature
70 °C

Procedure

To a solution of {3-[2-fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid (36B)(0.044 g, 0.10 mmol) in methanol (2 ml) was added concentrated sulfuric acid (0.25 ml) and heated at 70° C. for 90 minutes before being cooled to rt. The reaction mixture was then concentrated in vacuo, diluted with water (5 ml) an extracted with ethyl acetate (2×10 ml). The organic layer was then dried over magnesium sulfate and concentrated in vacuo to afford a colourless oil. Single peak in LC-MS, (42 mg, 91% purity) and required no further purification; m/z (LC-MS, ESP), RT=3.31 mins (M+H) 453;

Workup

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

Sources & evidence

ORD record
ord-1f3021c486784991b0f4f25a51f255ae
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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