Hydrochloric Acid → HCID 25099970, compound

HRID 1013295Notes

Reaction equation

HRID 1013295 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[C:9]2[C:31]([O:33]CC)=[O:32])=[CH:5][CH:4]=1.[Li+].[OH-].Cl>O1CCCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[C:9]2[C:31]([OH:33])=[O:32])=[CH:36][CH:37]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67315446HCID 67315446, compound

Product 1

HCID 25099970HCID 25099970, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 101C (80 mg) in tetrahydrofuran (2 ml), methanol (1 ml) and water (1 ml) was added LiOH (100 mg). The mixture was stirred at room temperature overnight. The mixture was then acidified with 5% HCl and extracted with ethyl acetate (200 ml). The organic layer was washed with water, brine and dried over Na2SO4. After concentration of the solvent, the residue was dissolved in DMSO/methanol (1:1, 1.5 ml) and purified via reverse phase HPLC. 1H NMR (500 MHz, dimethyl sulfoxide-d6) δ 12.99 (m, 1H), 8.01 (m, 1H), 7.86 (m, 1H), 7.73 (m, 1H), 7.46 (m, 6H), 7.27 (m, 1H), 6.98 (m, 3H), 6.74 (m, 2H), 5.70 (s, 2H), 4.64 (m, 2H), 4.48 (m, 2H), 3.67 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (200 ml)
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. dissolutionAfter concentration of the solvent, the residue was dissolved in DMSO/methanol (1:1, 1.5 ml)
  5. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-5edbc4116441413994b089573ed212c6
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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