Ethanol → (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

HRID 879275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879275
C([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20]([NH2:22])[S:21][C:17]=2[C:16]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C(C)(C)C.CCO.C1COCC1>O>[NH2:22][C:20]1[S:21][C:17]2[C:16]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)=[C:15]([C@H:9]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:8][OH:7])[C:24]([CH3:25])=[CH:23][C:18]=2[N:19]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 86699790(S)-2-(2-Amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Produkt 1

HCID 86699791(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanolAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A flask was charged with (S)-2-(2-Amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (2.15 g, 4.52 mmol), LiOH monohydrate (2.00 g, 47.4 mmol), H2O (4 mL), EtOH (absolute, 4.0 mL), and THF (8.0 mL). The reaction was placed under N2 and heated to 100° C. After 2 h, the reaction was cooled to 23° C., diluted with H2O, and extracted with EtOAc several times. The combined organic phases were dried (Na2SO4), filtered, and concentrated. The residue was treated with benzene and purified via chromatography on silica gel (80 g “gold” ISCO column; Hex/EtOAc) giving (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol (1.10 g, 62% yield). LCMS-ESI+: calc'd for C20H23ClN2O2S: 391.1 and 393.1 (M+H+); found: 391.2 and 393.2 (M+H+). 1H-NMR: 400 MHz, (CDCl3) δ: 7.49-7.41 (m, 2H), 7.36-7.32 (m, 2H), 7.20 (d, J=7.3 Hz, 1H), 5.39 (s, broad, 2H), 4.52-4.50 (m, 1H), 3.85-3.70 (m, 2H), 2.63 (s, 3H), 0.99 (s, 9H).

Aufarbeitung

  1. temperaturethe reaction was cooled to 23° C.
  2. extractionextracted with EtOAc several times
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was treated with benzene
  7. custompurified via chromatography on silica gel (80 g “gold” ISCO column; Hex/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-cd9da8a3ae59446eb71a84c9dabf3ba1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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