Triethylamine → (1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 517018노트

반응식

HRID 517018 반응식
C(N(CC)CC)C.[I-].[CH2:9]([O:11][C:12]([C@@:14]1([NH:19][C:20](N2C=C[N+](C)=C2)=[O:21])[CH2:16][C@H:15]1[CH:17]=[CH2:18])=[O:13])[CH3:10].[CH2:28]([N:34]([CH3:43])[C:35]([C@@H:37]1[CH2:41][C@@H:40]([OH:42])[CH2:39][NH:38]1)=[O:36])[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33]>C(Cl)Cl>[CH2:9]([O:11][C:12]([C@@:14]1([NH:19][C:20]([N:38]2[CH2:39][C@H:40]([OH:42])[CH2:41][C@H:37]2[C:35](=[O:36])[N:34]([CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:43])=[O:21])[CH2:16][C@@H:15]1[CH:17]=[CH2:18])=[O:13])[CH3:10]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 57816715(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamideHCID 866332061-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide

생성물 1

HCID 66650543(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (1.3 mL, 3 eq.) was added at room temperature under nitrogen to a mixture of 1-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide 34 (0.7 g, 1 eq.) and compound 49 (1.2 g, 1 eq.) in DCM (15 mL). The reaction mixture was stirred overnight at room temperature and then quenched with 1M aqueous hydrochloric acid. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 50 as a white solid in 70% yield. 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.10-1.14 (td, J=7.07 and 2.01 Hz, 3H), 1.15-1.17 (m, 1H), 1.22-1.30 (m, 1H), 1.33-1.41 (m, 2H), 1.42-1.50 (m, 1H), 1.54-1.57 (m, 1H), 1.71-1.79 (m, 1H), 1.97-2.07 (m, 4H), 2.74 (s, 1H), 2.97 (s, 2H), 3.11 (d, J=10.24 Hz, 1H), 3.15-3.21 (m, 1H), 3.43-3.48 (m, 1H), 3.91-4.07 (m, 2H), 4.29-4.30 (m, 1H), 4.65-4.69 (d, J=6.50 Hz, 1H), 4.90-4.96 (m, 3H), 5.00-5.06 (m, 2H), 5.19-5.25 (dd, J=17.04 and 6.50 Hz, 1H), 5.51-5.61 (m, 1H), 5.71-5.83 (m, 1H), 7.08 (s, 1H); MS (ESI): m/z=406 (MH−).

후처리

  1. customquenched with 1M aqueous hydrochloric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-19ac4bb586254624a2a6b1c4fd0dbda4
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115095B2

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