Acetic Acid → HCID 44365793, Verbindung

HRID 1292394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292394
C(OC([N:11]([CH2:37][CH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47]CC2C=CC=CC=2)=[CH:43][CH:42]=1)[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:24](=[O:28])[NH:25][CH2:26][CH3:27])[CH:21]=2)[NH:16][C:15]=1[C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[CH:30]=1)=O)C1C=CC=CC=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[OH-].[OH-].[Pd+2].O>[CH3:35][C:33]1[CH:34]=[C:29]([C:15]2[NH:16][C:17]3[C:22]([C:14]=2[CH2:13][CH2:12][NH:11][CH2:37][CH2:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][C:44]([OH:47])=[CH:45][CH:46]=2)=[CH:21][C:20]([O:23][C:24](=[O:28])[NH:25][CH2:26][CH3:27])=[CH:19][CH:18]=3)[CH:30]=[C:31]([CH3:36])[CH:32]=1

Komponenten

8

Edukt 3

HCID 176Acetic AcidHCID 86752673HCID 86752673, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 44365793HCID 44365793, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (12 mg in a mixture of 1.5 mL tetrahydrofuran and 0.5 mL methanol) was added 12 mg of 10% palladium hydroxide on carbon catalyst followed by acetic acid (0.010 mL of a 30% solution in water). The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 1.5 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (methylene chloride:methanol: ammonium hydroxide, 90:7:1) gave the title compound (8.2 mg). m/e=500 (M+H)

Aufarbeitung

  1. customevacuated
  2. customAfter 1.5 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (methylene chloride:methanol: ammonium hydroxide, 90:7:1)

Quellen und Nachweise

ORD-Eintrag
ord-ca669d22591c4466861e5aeae715b2d9
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756507

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