Triethylamine → N-[(2-Adamantyloxy)carbonyl]-alpha-methyl-D-tryptophan methyl ester

HRID 1781190

반응식

HRID 1781190 반응식
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12](Cl)=[O:13])[CH2:8]2.[CH3:15][O:16][C:17](=[O:31])[C@@:18]([CH3:30])([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[NH2:19].C(N(CC)CC)C>C1COCC1>[CH3:15][O:16][C:17](=[O:31])[C@@:18]([CH3:30])([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[NH:19][C:12]([O:11][CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)=[O:13]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 6923819Methyl alpha-methyl-D-tryptophanateHCID 108785372-adamantyl Chloroformate

생성물 1

HCID 14802502N-[(2-Adamantyloxy)carbonyl]-alpha-methyl-D-tryptophan methyl ester수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred solution of 2-adamantylchloroformate (0.965 g, 4.5 mmol) in dry THF (10 mL) was added a solution of α-methyl-D-tryptophan methyl ester (0.928 g, 4 mmol) in dry THF (20 mL) followed by a solution of triethylamine (0.808 g, 8 mmol) in dry THF (20 mL) dropwise. After 15 minutes, the reaction mixture was filtered, the solvent removed in vacuo and column chromatographed using 2% MeOH:98% CH2Cl2 as eluant to yield the title compound (1.42 g, 89%) as a syrup. IR (film) 1740-1695 b.r cm-1 ; NMR (CDCl3) δ1.50-1.60 (2H, m), 1.67 (3H, s), 1.70-2.10 (12H, m), 3.38 (1H, d, J=14.5 Hz), 3.50-3.60 (1H, br.s), 3.68 (3H, s), 4.86 (1H, br.s), 5.28 (1H, br.s), 6.93 (1H, d, J 2.4 Hz); 7.04-7.10 (2H, m), 7.33 (1H, d, J 8.2 Hz) 7.54 (1H, d, J 7.8 Hz), 8.18 (1H, br.s).

후처리

  1. filtrationthe reaction mixture was filtered
  2. customthe solvent removed in vacuo and column
  3. customchromatographed

출처 및 근거

ORD 기록
ord-d93af08881164c99bf70705b0ae41ad0
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05631281

연결된 노트

불러오는 중…