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

HRID 1092570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092570
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-a261e596078d4bea965bc30129a9d573
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129417B2

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