Hydrochloric Acid → HCID 11511422, compound

HRID 2244030Notes

Reaction equation

HRID 2244030 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([OH:30])[C:22]=3[CH2:31][CH2:32][CH3:33])[N:14]=2)=[O:12])[CH:5]=1.CO.[OH-].[Li+].[ClH:39]>O1CCCC1>[ClH:39].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([C:11](=[O:12])[NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([OH:34])=[O:2])[CH:5]=3)[N:14]=2)=[C:22]([CH2:31][CH2:32][CH3:33])[C:23]=1[OH:30])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68430670HCID 68430670, compound

Product 1

HCID 11511422HCID 11511422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-{[6-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-pyridine-2-carbonyl]-amino}-benzoic acid methyl ester (700 mg, 1.51 mmol) in minimal amount of tetrahydrofuran (2 mL), add methanol (8 mL), and 2N aqueous lithium hydroxide solution (2.27 mL, 4.54 mmol) and stir 30 hours. Add 1N hydrochloric acid (50 mL), collect resultant white solid by filtration to yield the title compound (493 mg, 1.02 mmol): 1H NMR (DMSO-d6) δ 0.90 (t, 3H), 1.54 (m, 2H), 2.57 (s, 3H), 2.67 (m, 2H), 5.51 (s, 2H), 6.77 (d, 1H), 7.73 (m, 2H), 7.85 (d, 1H), 8.13 (m, 3H), 8.51 (m, 1H), 10.66 (s, 1H), 12.86 (s, 1H), 13.05 (br s, 1H): MS (m/z): 447 (M-HCl−1).

Workup

  1. customcollect resultant white solid
  2. filtrationby filtration

Sources & evidence

ORD record
ord-de47dbdfa1e24e219d5c1f0973a47ddd
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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