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

HRID 2244036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244036
[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]

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c3199a480cb649e485c0fe74489d3f20
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678794B2

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