Hydrochloric Acid → HCID 90289953, Verbindung

HRID 1471631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471631
[C:1](=O)([S:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:14]([N:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH3:17])=[O:15])[CH:7]=1)[CH3:2].[OH-].[K+].C([N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=C1CBr)(=O)C.Cl>C(O)C>[C:30]([O:29][C:27]([NH:26][C@H:13]([C:14]([N:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH3:17])=[O:15])[CH2:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][CH2:4][S:3][CH2:1][C:2]1[NH:40][C:48]2[C:43]([C:42]=1[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:28])([CH3:31])([CH3:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10860687HCID 10860687, VerbindungHCID 90327418HCID 90327418, Verbindung

Produkt 1

HCID 90289953HCID 90289953, VerbindungAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (S)—S-3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenethyl ethanethioate (2.8 g, 5.74 mmol) in ethanol (20 ml) was added potassium hydroxide (0.64 g, 11.4 mmol). After 10 minutes, ethyl 2-(1-acetyl-2-(bromomethyl)-1H-indol-3-yl)acetate (2.2 g, 6.47 mmol) was added to the solution. The reaction was stirred for 2 hours at room temperature. The reaction was neutralized with 1N (aq) HCl and then extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (3-6% MeOH/DCM) to provide the desired product (2.0 g, 3.0 mmol), 52.3%. MS (m/z) 660 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude product was introduced to a silica gel loading column
  6. custompurified by column chromatography (3-6% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-108dfab399ca454ca8805acf02c5e8f7
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012441B2

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