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Sodium Hydroxide → (3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acid

HRID 881667
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Reaktionsgleichung

Reaktionsgleichung von HRID 881667
C[O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)[CH:6]=1.[OH-].[Na+]>CO>[C:36]1([CH:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:25])([F:26])[F:27])[CH:18]=2)[CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:42])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68908942(3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester

Produkt 1

HCID 68910862(3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (4c). (0.58 g, 0.001 mol) in methanol (7.5 mL) was treated with 2N NaOH (5.0 ml) and the mixture stirred overnight at ambient temperature. After concentration to dryness, the residue was dissolved in EtOAc (25 mL) and water was added (10 mL), the solution acidified to pH 3 with concentrated hydrochloric acid, then extracted into EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, and then concentrated in vacuo to provide the carboxylic acid as waxy oil (5c) 0.5 g in 89% yield. 1H NMR (CD3OD) δ 7.22 (m, 12H), 7.05 (d, 1H), 7.01 (d, 1H), 6.98 (s, 1H), 6.63 (d, 1H), 6.61 (s, 1H), 6.57 (d, 1H), 4.22 (t, 1H), 3.61 (s, 2H), 3.58 (t, 2H), 3.54 (s, 2H), 3.11 (d, 2H), 2.63 (t, 2H), 1.79 (t, 2H); 13C NMR (CD3OD) δ 175.7, 160.4, 150.4, 145.0, 143.9, 137.3, 130.6, 130.5, 130.2, 129.5, 129.2, 128.6, 127.3, 122.4, 120.9, 120.3, 116.5, 114.1, 66.3, 60.9, 59.6, 58.3, 51.6, 51.1, 42.2, 27.9. Anal. Calcd for C33H32F3NO4: C, 70.32; H, 5.72; N, 2.49; F, 10.11. Found: C, 70.05; H, 5.93; N, 2.58; F, 9.84.

Aufarbeitung

  1. concentrationAfter concentration to dryness
  2. dissolutionthe residue was dissolved in EtOAc (25 mL)
  3. additionwater was added (10 mL)
  4. extractionextracted into EtOAc (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d082bc28116d4d2899edb506de7decd1
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993628B2

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