Hydrochloride methanol → HCID 23517381, compound

HRID 1835989Notes

Reaction equation

HRID 1835989 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=[O:19])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1.Cl.[CH3:22]O>>[CH3:22][O:19][C:18]([C:4]1[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=[C:2]([OH:1])[CH:3]=1)=[O:20]

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 22221627HCID 22221627, compound

Product 1

HCID 23517381HCID 23517381, compoundYield 47%

Procedure

A solution of carboxylic acid 24 (0.35 g, 1.3 mmol) in HCl/MeOH(10 ml) was refluxed for 2 hr. The reaction was then cooled, concentrated and the product was dissolved in EtOAc, washed with sat NaHCO3, seperated dried, and concentrated to give a solid. The solid was triturated with CH2Cl2, filtered to give a solid (0.15 g, 47%): Mp=236-238° C.; 1NMR (DMSO-d6) δ 9.90 (s, 1 H), 9.57 (s, 1 H), 7.73 (d, 2 H, J=8.5 Hz), 7.23 (d, 1 H, J=2.1 Hz), 7.17 (d. 1 H, J=2.1 Hz),7.12 (s, 1 H), 6.88 (d, 2 H, J=8.5 Hz), 3.94 (s, 3 H); MS 283 (M−H)−

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated
  3. dissolutionthe product was dissolved in EtOAc
  4. washwashed
  5. customseperated
  6. customdried
  7. concentrationconcentrated
  8. customto give a solid
  9. customThe solid was triturated with CH2Cl2
  10. filtrationfiltered

Sources & evidence

ORD record
ord-eea6c7e1006c467f8805051915faa66e
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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