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Dichloromethane → N-[(2S)-2-amino-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide

HRID 1062893
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1062893
C(OC([NH:8][C@@H:9]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:10][NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH3:13])=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>C(O)C>[NH2:8][C@@H:9]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:10][NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][CH:25]([CH3:26])[CH3:27])=[O:22])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH3:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69734334N-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide

Produkt 1

HCID 69735335N-[(2S)-2-amino-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide (84 mg, 0.176 mmol) is stirred with 1 mL of trifluoroacetic acid and 3 mL of dichloromethane for 30 min. It is then concentrated on a rotary evaporator and then neutralized with several mL of saturated aqueous sodium bicarbonate. The product is taken up in 70 mL of ethyl ether, washed with several more mL of bicarbonate solution, and then dried over anhydrous sodium sulfate. Concentration from ethyl ether, and then from absolute ethanol, afforded 75 mg of a slightly yellow oil, whose NMR spectrum was consistent with the title compound, along with a small amount of residual ethanol. NMR (CDCl3) δ 7.96 (d, J=9 Hz, 1H), 7.3-7.17 (m, 5H), 6.88 (br t, 1H), 4.13 (m, 1H), 3.27 (m, 1H), 3.13 (m, 1H), 3.05 (m, 1H), 2.94 (m, 1H), 3.83 (m, 2H), 2.7 (dd, 1H), 2.57 (dd, 1H), 2.08 (m, 1H), 1.72 (m, 1H), 1.31 (d, J=7 Hz, 3H), 0.93-0.86 (overlapping d, 12H).

Aufarbeitung

  1. concentrationIt is then concentrated on a rotary evaporator
  2. washwashed with several more mL of bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationConcentration from ethyl ether
  5. customfrom absolute ethanol, afforded 75 mg of a slightly yellow oil, whose NMR spectrum

Quellen und Nachweise

ORD-Eintrag
ord-0a6de3c3574041d6b35cf901dc577e8a
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06962934B2

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