Hydrochloric Acid → HCID 53810310, Verbindung

HRID 263507

Reaktionsgleichung

Reaktionsgleichung von HRID 263507
[C:1]([S:4][C@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([O:9]C)=[O:8])(=O)[CH3:2].[OH-].[Na+].Br[C:28]1[CH:33]=C[CH:31]=[C:30](C)[C:29]=1[CH3:35].Cl.[CH3:37]O>>[CH3:37][C@:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])([C@H:5]([S:4][CH2:1][C:2]1[CH:31]=[CH:30][C:29]([CH3:35])=[CH:28][CH:33]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 684723-Bromo-o-xyleneHCID 15747430HCID 15747430, Verbindung

Produkt 1

HCID 53810310HCID 53810310, VerbindungAusbeute 79 %

Versuchsvorschrift

The acetylated thiol 17 (500 mg, 1.4 mmol) was dissolved in methanol (2 mL) and NaOH was added (1.6 mL, 1M aqueous), followed by bromoxilene (300 mg, 1.62 mmol). After 20 min most of the starting material has disappeared (monitored by TLC). The solution was carefully neutralized with dilute HCl. The volatiles were removed in vacuo and the residue was extracted with Cl2CH2 (3×) The organic layer was washed with brine and dried over Na2SO4. The crude product was purified by flash column chromatography (silica, 5% to 20% ethyl acetate/hexane) to give the desired ester 18 (480 mg, 79%) as a white solid, which crystallized. mp 97°-98° C. (ether-hexane); [α]20D =-171.8° (c=1.05, CHCl3); 1H NMR (CDCl3).δ1.384 (s, 9H), 2.326 (s, 3H), 3.393 (d, J=13 Hz, 1H), 3.551 (d, J=13 Hz, 1H), 3.572 (s, 3H, OCH3), 4.126 (d,J=5.4 Hz, H-3), 4.630 (dd, J=8.8, 5.8 Hz, 1H, H-2), 5.220 (bd, J=8.8 Hz, 1H, H--N), 7.028-7.107 (m, 4H), 7.291-7.362 (m, 5H); 13C NMR (CDCl3).δ21.0, 28.3, 35.5, 51.6, 52.1, 57.5, 80.1, 127.8, 128.5, 128.7, 128.9, 129.2, 134.3, 136.9, 138.4, 154.7, 170.8; MS m/z 316 [M+H]+ ; Anal. Calcd for C23H29O4NS.1/4H2O: C, 65.76; H, 7.08; N, 3.33. Found: C, 65.59; H, 7.03; N, 3.36.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. extractionthe residue was extracted with Cl2CH2 (3×) The organic layer
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by flash column chromatography (silica, 5% to 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bb2a4022d2914891b745ddac85c139dd
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643872

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