Triethylamine → tert-butyl (1S)-1-[(4-benzyl-2-vinyl-1-piperazinyl)carbonyl]-3-butenylcarbamate

HRID 1060615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060615
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH:25]([CH:29]=[CH2:30])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC>C(Cl)Cl>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH:14]=[CH2:15])=[O:12])[CH:25]([CH:29]=[CH2:30])[CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acidHCID 146122431-Benzyl-3-vinylpiperazine

Produkt 1

HCID 10200953tert-butyl (1S)-1-[(4-benzyl-2-vinyl-1-piperazinyl)carbonyl]-3-butenylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(2S)-2-[(tert-butoxycarbonyl)amino]-4-pentenoic acid (466 mg, 2.17 mmol) and 1-benzyl-3-vinylpiperazine (436 mg, 2.17 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiinide hydrochloride (HOBT, 622 mg, 3.26 mmol) were combined with anhydrous CH2Cl2 (10 mL) at room temperature. Et3N (0.74 mL, 5.43 mmol) was added in one portion. The resulted solution was maintained at room temperature for 18 h at which time it was concentrated in vacuo to a volume of approximately 5 mL. Then the solution was purified by silica gel chromatography (SGC) eluting with 2:1 hex-EtOAc. The title compound (a pair of diastereomers) was obtained (171 mg, 20%) as a pale-yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.31 (s, 5H), 5.99-5.82 (m, 1H), 5.81-5.65 (m, 1H), 5.50-5.00 (m, 6H), 4.75-4.23 (m, 2H), 3.70-3.37 (m, 3H), 3.11-2.79 (m, 2H), 2.59-2.00 (m, 4H), 1.42 (s, 9H) ppm. MS (CI) 400.6 (M+H).

Aufarbeitung

  1. concentrationwas concentrated in vacuo to a volume of approximately 5 mL
  2. customThen the solution was purified by silica gel chromatography (SGC)
  3. washeluting with 2:1 hex-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-1da030e96ed8440780d110745342b578
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525044B2

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