Diisopropylethylamine → (3-{[(Benzo[1,2,5]oxadiazole4-sulfonyl)-(4-butyl-benzyl)-amino]-methyl}-phenyl)-acetic acid methyl ester

HRID 890786

Reaktionsgleichung

Reaktionsgleichung von HRID 890786
[N:1]1[O:5][N:4]=[C:3]2[C:6]([S:10](Cl)(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[CH3:14][O:15][C:16](=[O:37])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH3:36])=[CH:29][CH:28]=2)[CH:19]=1.C(N(CC)C(C)C)(C)C>ClCCCl.CCOC(C)=O>[CH3:14][O:15][C:16](=[O:37])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]([S:10]([C:6]2[C:3]3=[N:4][O:5][N:1]=[C:2]3[CH:9]=[CH:8][CH:7]=2)(=[O:12])=[O:11])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH3:36])=[CH:29][CH:28]=2)[CH:19]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 27354462,1,3-Benzoxadiazole-4-sulfonyl chlorideHCID 54268705(3-((4-Butyl-benzylamino)-methyl)-phenyl)-acetic acid methyl ester

Produkt 1

HCID 69544491(3-{[(Benzo[1,2,5]oxadiazole4-sulfonyl)-(4-butyl-benzyl)-amino]-methyl}-phenyl)-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Benzofurazan-4-sulfonyl chloride (109 mg, 0.50 mmol) was added to a solution of {3-[(4-butyl-benzylamino)-methyl]-phenyl}-acetic acid methyl ester (163 mg, 0.50 mmol) and N,N-diisopropylethylamine (65 mg, 0.50 mmol) in 1,2-dichloroethane. The reaction mixture was stirred at room temperature for 20 h. The reaction was diluted with EtOAc and the organic solution was washed with water followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated to afford (3-{[(benzo[1,2,5]oxadiazole-4-sulfonyl)-(4-butyl-benzyl)-amino]-methyl}-phenyl)-acetic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 7.95 (d, 1H), 7.88 (d, 1H), 7.37–7.41 (m, 1H), 7.06–7.10 (m, 2H), 6.90–6.97 (m, 6H), 4.56 (s, 2H), 4.51 (s, 2H), 3.66 (s, 3H), 3.45 (s, 2H), 2.48 (t, 2H), 1.45–1.53 (m, 2H), 1.23–1.32 (m, 2H), 0.89 (t, 3H); MS 508 (M+18).

Aufarbeitung

  1. washthe organic solution was washed with water
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b18d816721d64d0da63f528d21467f60
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998423B2

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