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

HRID 1092570ノート

反応式

HRID 1092570 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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)+.

後処理

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

出典と根拠

ORDレコード
ord-a261e596078d4bea965bc30129a9d573
出典データセット
uspto-grants-2012_03
特許番号
US08129417B2

反応ノート

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