Potassium Hydroxide → HCID 9939669, Verbindung

HRID 1954276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1954276
C[O:2][C:3]([C:5]1[C:9]([O:10][CH3:11])=[C:8]([S:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:34]4[C:33]([CH3:35])=[C:32]([CH3:36])[S:31][C:30]=4[C:29]([Br:37])=[C:28]4[C:23]=3[CH:24]=[CH:25][CH:26]=[CH:27]4)=[CH:18][C:17]=2[CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)(=[O:14])=[O:13])[S:7][CH:6]=1)=[O:4].[OH-].[K+]>C1COCC1.CO>[Br:37][C:29]1[C:30]2[S:31][C:32]([CH3:36])=[C:33]([CH3:35])[C:34]=2[C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][S:12]([C:8]3[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:9]=3[O:10][CH3:11])(=[O:14])=[O:13])=[C:17]([CH:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH:18]=2)=[C:23]2[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]2

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 54249985HCID 54249985, Verbindung

Produkt 1

HCID 9939669HCID 9939669, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

At ambient temperature, to a stirred solution of 5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester (0.722 g, 1.05 mmol) in THF:MeOH (3:2, 10 mL) was added 1N KOH (5.26 mL). After 1.5 h, the reaction was quenched with 1N HCl (40 mL) and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated. Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil, eluting with 25% EtOAc/hexane gave 0.596 g (85%) of the title compound as a white solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.34-1.39 (m, 2 H), 1.49-1.54 (m, 5 H), 1.62-1.73 (m, 3 H), 1.79-1.83 (m, 1 H), 2.43 (s, 3 H), 3.23 (quintet, 1 H), 3.97 (s, 3 H), 7.24 (dd, 1 H), 7.30 (d, 1 H), 7.34-7.36 (m, 2 H), 7.49 (t, 1 H), 7.64 (t, 1 H), 8.19 (d, 1 H), 8.72 (s, 1 H), 13.34 (br. s, 1 H). IR (KBr) 3400, 2950, 1690, 1375 and 860 cm-1. mass spectrum (-ESI), m/z 669/671 (M-H). Anal. Calcd. for C31H27BrO6S3 : C, 55.44; H, 4.05 N, 0.00. Found: C, 55.25; H, 4.11 N, 0.01.

Aufarbeitung

  1. customthe reaction was quenched with 1N HCl (40 mL)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on 2% H3PO4 /MeOH treated Biotage KP-Sil
  6. washeluting with 25% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-0fe03e3810584fe78deff384ef045ac1
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121271

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