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

HRID 881668
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Reaktionsgleichung

Reaktionsgleichung von HRID 881668
C[O:2][C:3](=[O:39])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:25][CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[CH:6]=1.[OH-].[Na+]>CO>[C:27]1([CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:25][N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:39])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68908406(3-{3-[(2,2-Diphenyl-ethyl)-(3-methoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester

Produkt 1

HCID 68906747(3-{3-[(2,2-Diphenyl-ethyl)-(3-methoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (3-{3-[(2,2-Diphenyl-ethyl)-(3-methoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (4d). (0.2 g, 0.00038 mol) in methanol (5 mL) was treated with 2N NaOH (2.5 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. Solidification of the waxy oil from pet. ether gave white solid (5d) 0.16 g in 84% yield, mp: 42.1° C. 1H NMR (CD3OD) δ 7.39 (t, 1H), 7.28 (m, 111H), 7.07 (d, 1H), 7.03 (t, 2H), 6.89 (d, 1H), 6.69 (s, 1H), 6.67 (s, 1H), 4.46 (t, 1H), 4.40 (s, 1H), 4.09 (d, 2H), 3.97 (s, 2H), 3.76 (s, 3H), 3.62 (t, 2H), 3.57 (s, 1H), 3.30 (t, 2H), 2.24 (t, 1H), 1.99 (d, 1H); 13C NMR (CD3OD) δ 175.3, 161.9, 159.6, 141.4, 137.6, 131.7, 130.6, 130.5, 130.3, 128.8, 128.7, 124.2, 123.6, 117.7, 117.0, 116.3, 116.7, 114.0, 105.2, 66.7, 59.6, 58.3, 55.9, 53.9, 41.9, 24.7. Anal. Calcd for C33H35NO4.2.5H2O: C, 71.45; H, 6.36; N, 2.52. Found: C, 71.16; H, 6.83; N, 2.43.

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-f26d5006701140d393c40a2c64b2d16e
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993628B2

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