Hydrochloric Acid → HCID 25143778, compound

HRID 576246Notes

Reaction equation

HRID 576246 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 1:1 DMSO/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 1:1 DMSO/methanol
  7. custompurified by reverse phase HPLC (C18, 20 to 100% acetonitrile/water/0.1% TFA)

Sources & evidence

ORD record
ord-78b0df0a1dba4422906ae899931a7adb
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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