Hydrochloric Acid → HCID 25143778, compound

HRID 2095244Notes

Reaction equation

HRID 2095244 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[C:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[O:31][CH3:32])[CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[C:33]([O:35]CC)=[O:34])=[CH:4][CH:3]=1.O[Li].O.Cl>C1COCC1.CO.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[C:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[O:31][CH3:32])[CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[C:33]([OH:35])=[O:34])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68936098HCID 68936098, compound

Product 1

HCID 25143778HCID 25143778, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 65A (70 mg) in THF (2 mL), methanol (1 mL) and water (1 mL) was treated with LiOH.H2O (100 mg) and stirred at ambient temperature overnight. The mixture was acidified with 5% aqueous HCl and extracted with ethyl acetate. The extract was washed with water, brine and dried (Na2SO4), filtered and concentrated. The concentrate was dissolved in 1:1DMSO/methanol and purified by reverse phase HPLC (C18, 20 to 100% acetonitrile/water/0.1% TFA). 1H NMR (300 MHz, CDCl3) δ 8.72 (s, 1H), 8.38 (dd, 1H), 8.15 (dd, 1H), 7.72 (d, 1H), 7.35-7.57 (m, 5H), 7.08-7.21 (m, 3H), 6.65 (d, 1H), 4.18 (t, 2H), 3.82 (s, 3H), 3.47 (t, 2H), 2.37 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in 1:1DMSO/methanol
  7. custompurified by reverse phase HPLC (C18, 20 to 100% acetonitrile/water/0.1% TFA)

Sources & evidence

ORD record
ord-7f994fc7b6324b1693a32170d6b0cb35
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

Loading…