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

HRID 2363543노트

반응식

HRID 2363543 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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)+.

후처리

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

출처 및 근거

ORD 기록
ord-072a40e6247d4b97b7e259175f1b171c
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691865B2

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