(S,E)-tert-butyl 3-(3-(2-(tert-butoxycarbonylamino)butanamido)prop-1-enyl)-1H-indole-1-carboxylate → 3-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1039027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039027
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:32][CH3:33])[C:10]([NH:12][CH2:13]/[CH:14]=[CH:15]/[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:17]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:28]([O:27][C:25]([N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][CH2:14][CH2:13][NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:32][CH3:33])=[CH:17]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

Komponenten

4

Edukt 1

HCID 67235756(S,E)-tert-butyl 3-(3-(2-(tert-butoxycarbonylamino)butanamido)prop-1-enyl)-1H-indole-1-carboxylate

Produkt 1

HCID 672353373-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A 250 mL Parr hydrogenation vessel was charged with (S,E)-tert-butyl 3-(3-(2-(tert-butoxycarbonylamino)butanamido)prop-1-enyl)-1H-indole-1-carboxylate (280 mg, 0.42 mmol), 10% palladium on carbon (34 mg), and ethanol (6.0 mL). The vessel was evacuated and filled with hydrogen. This was repeated two more times. The vessel was then filled with 50 psi hydrogen. After 24 h, the resulting solution was filtered through CELITE and the filtrate concentrated in vacuo to yield 3-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]indole-1-carboxylic acid tert-butyl ester. 1H NMR (300 MHz, CDCl3) δ 7.21-7.24 (m, 1H), 7.07-7.12 (m, 1H), 6.64-6.71 (m, 1H), 6.42-6.46 (m, 1H), 4.38-4.45 (m, 1H), 3.39-3.53 (m, 2H), 2.53 (t, J=6.8 Hz, 2H), 1.67-1.96 (m, 4H), and 0.88-0.93 (m, 3H).

Aufarbeitung

  1. customThe vessel was evacuated
  2. additionfilled with hydrogen
  3. additionThe vessel was then filled with 50 psi hydrogen
  4. filtrationthe resulting solution was filtered through CELITE
  5. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d14e30e998d4ccab349a3cbfe997782
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552032B2

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