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Ethanethiol → ethyl ((1S)-5-{3-[2-hydroxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235899
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2235899
C[O:2][C:3]1[CH:28]=[C:27]([C:29]2[S:30][C:31]3[CH2:37][CH2:36][CH2:35][CH2:34][C:32]=3[N:33]=2)[CH:26]=[CH:25][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]2.[Al+3].[Cl-].[Cl-].[Cl-].C(S)C>C(Cl)Cl>[OH:2][C:3]1[CH:28]=[C:27]([C:29]2[S:30][C:31]3[CH2:37][CH2:36][CH2:35][CH2:34][C:32]=3[N:33]=2)[CH:26]=[CH:25][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]2
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Komponenten

5

Edukt 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 16110464ethyl ((1S)-5-{3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Produkt 1

HCID 59300497ethyl ((1S)-5-{3-[2-hydroxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

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Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl ((1S)-5-{3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 164, 400 mg, 0.787 mmol) dissolved in CH2Cl2 (10 mL) was added AlCl3 (511.2 mg, 3.834 mmol), and then the solution was cooled to 0° C. Ethanethiol (0.284 mL, 3.834 mmol) was added dropwise to the solution which was stirred at 0° C. for 3 h. The reaction mixture was poured onto ice-water (20 mL) with vigorous stirring. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The crude material was purified by preparative HPLC, giving the desired product as a white solid (180.0 mg, 46%). 1H NMR (400 MHz, DMSO-d6): δ 9.27 (s, 1H), 7.28 (d, 1H), 7.20 (dd, 1H), 7.05 (d, 1H), 6.96 (d, 1H), 6.79 (s, 1H), 6.69 (dd, 1H), 4.07-4.18 (m, 6H), 3.39 (m, 1H), 2.72 (dd, 6H), 2.09-2.20 (m, 5H), 1.80-1.59 (m, 5H), 1.18 (t, 3H).

Aufarbeitung

  1. additionThe reaction mixture was poured onto ice-water (20 mL) with vigorous stirring
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cf59aa59bc9d4ac1859cb3b0841a96d8
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07714004B2

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