Hydrochloric Acid → N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acid

HRID 2244036Notes

Reaction equation

HRID 2244036 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:36])[C:6]1[CH:35]=[CH:34][CH:33]=[C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=3[CH2:30][CH2:31][CH3:32])[CH:13]=2)=[O:10])[CH:7]=1.Cl>O1CCCC1.C(O)C.O>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:7]=[C:6]([CH:35]=[CH:34][CH:33]=3)[C:5]([OH:36])=[O:4])[CH:17]=[CH:16][CH:15]=2)=[C:21]([CH2:30][CH2:31][CH3:32])[C:22]=1[OH:29])(=[O:28])[CH3:27]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68429187N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acid methyl ester

Product 1

HCID 11561413N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acidYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 1N lithium hydroxide (20 mL) to a solution of N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acid methyl ester (1.75 g, 3.79 mmol) in tetrahydrofuran (15 mL) and ethanol (10 mL). Stir overnight at room temperature. Dilute with water. Acidify with 1N hydrochloric acid. Concentrate to remove organic solvents; filter and wash with water several times, then with hexanes. Dry to afford the title compound as an off-white powder (1.54 g, 91%): 1H NMR (DMSO-d6) δ 0.89 (t, 3H), 1.51 (sextet, 2H), 2.58 (s, 3H), 2.63 (t, 2H), 5.27 (s, 2H), 6.74 (d, 1H), 7.20 (d, 1H), 7.40 (t, 1H), 7.65-7.71 (m, 2H), 7.81 (d, 1H), 7.97 (s, 1H), 8.14 (d, 1H), 8.18 (d, 1H), 8.52 (s, 1H), 10.51 (s, 1H), 12.85 (s, 1H), 13.43 (bs, 1H); MS (APCI-neg mode) m/z (rel intensity) 446 (100).

Workup

  1. concentrationConcentrate
  2. customto remove organic solvents
  3. filtrationfilter
  4. washwash with water several times
  5. customDry

Sources & evidence

ORD record
ord-c3199a480cb649e485c0fe74489d3f20
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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