1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-methyl 4-(tert-butoxycarbonylamino)-5-(4-iodobenzylamino)-5-oxopentanoate

HRID 333129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333129
Cl.[I:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH3:11][C:12]([O:15][C:16]([NH:18][C@H:19]([C:26](O)=[O:27])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:17])([CH3:14])[CH3:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:12]([O:15][C:16]([NH:18][C@H:19]([C:26]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([I:2])=[CH:4][CH:5]=1)=[O:27])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:17])([CH3:13])([CH3:11])[CH3:14]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7018756(S)-2-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acidHCID 16217505(4-Iodophenyl)methanamine hydrochloride

Produkt 1

HCID 68630197(S)-methyl 4-(tert-butoxycarbonylamino)-5-(4-iodobenzylamino)-5-oxopentanoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-iodobenzylamine hydrochloride (2.965 g, 11.0 mmol), Boc-Glu(OMe)-OH.DCHA (4.426 g, 10.0 mmol), EDCI (2.301 g, 10.0 mmol), HOBt (1.351 g, 10.0 mmol) in DCM (100 mL) containing DIPEA (5.23 mL) was stirred at room temperature under nitrogen for 20 h. The reaction mixture was diluted with DCM, washed with 1N HCl, sat. NaHCO3 solution, and brine. The solvent was evaporated under reduced pressure to give a crude product, which was purified by flash chromatography eluting with hexane/ethyl acetate (3:1) to give (S)-methyl 4-(tert-butoxycarbonylamino)-5-(4-iodobenzylamino)-5-oxopentanoate (3.653 g, 77%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.65 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.4 Hz, 2H), 6.65 (s, 1H), 5.24 (brs, 1H), 4.39 (t, J=5.4 Hz, 2H), 4.15 (m, 1H), 3.70 (s, 3H), 2.57-2.37 (m, 2H), 2.20-2.11 (m, 1H), 1.99-1.90 (m, 1H), 1.44 (s, 9H); MS (ESI), 499 (M+Na)+.

Aufarbeitung

  1. washwashed with 1N HCl, sat. NaHCO3 solution, and brine
  2. customThe solvent was evaporated under reduced pressure
  3. customto give a crude product, which
  4. customwas purified by flash chromatography
  5. washeluting with hexane/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9e77cf35d80a4badbc364a6754987d85
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877970B2

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