Triethylamine → tert-Butyl N-(3-chloropropane-1-sulfonyl)-L-leucinate

HRID 2363543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363543
Cl.[NH2:2][C@@H:3]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(N(CC)CC)C.[Cl:22][CH2:23][CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[Cl:22][CH2:23][CH2:24][CH2:25][S:26]([NH:2][C@@H:3]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])(=[O:28])=[O:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 12451443tert-butyl (2S)-2-amino-4-methylpentanoate hydrochloride

Produkt 1

HCID 86641980tert-Butyl N-(3-chloropropane-1-sulfonyl)-L-leucinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 2-amino-4-methylpentanoate hydrochloride (0.516 g, 2.306 mmol) were dissolved in dichloromethane (15 mL) and triethylamine (1.061 mL, 7.61 mmol) was added. 3-Chloropropane-1-sulfonyl chloride (0.337 mL, 2.77 mmol) was added dropwise, and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo, and the crude material was taken up in ether, filtered, and concentrated to give (S)-tert-butyl 2-(3-chloropropylsulfonamido)-4-methylpentanoate: 1H NMR (300 MHz, CDCl3) δ ppm 4.70 (d, J=9.7, 1H), 4.02-3.91 (m, 1H), 3.77-3.60 (m, 2H), 3.25-2.96 (m, 3H), 2.31 (tdd, J=2.2, 6.6, 9.2, 2H), 1.83 (dq, J=6.5, 13.0, 1H), 1.58-1.53 (m, 8H), 1.38 (t, J=7.3, 1H), 0.96 (dd, J=2.1, 6.6, 6H); MS (ESI+) m/z 345 (M+NH4)+.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-072a40e6247d4b97b7e259175f1b171c
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691865B2

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