Trifluoroacetic acid → 4-{[(5-Benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylamine

HRID 990079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990079
[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:31]=[CH:30][C:19]([CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[O:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl.CO>[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH2:21][NH2:22])=[CH:30][CH:31]=2)=[O:15])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 12044207Tert-butyl 4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylcarbamate

Produkt 1

HCID 120442084-{[(5-Benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylamineAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the sulfoxide of Example 21 (0.92 g, 2.04 mmol) in dichloromethane (14 mL) and methanol (2 drops) was added trifluoroacetic acid (3.5 mL). This mixture was stirred for 4 h, and TLC indicated the absence of starting material. The volatile components were removed in vacuo and the residue was taken up into dichloromethane (50 mL) and washed with dilute aqueous sodium bicarbonate (2×). The organic phase was dried (Na2SO4), filtered and completely evaporated to leave 0.71 g of pure title compound.

Aufarbeitung

  1. customThe volatile components were removed in vacuo
  2. washwashed with dilute aqueous sodium bicarbonate (2×)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customcompletely evaporated

Quellen und Nachweise

ORD-Eintrag
ord-db7b0ffd82cd4fa8a0ed920586864ef9
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458817B1

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