Triethylamine → tert-butyl (1S)-1-[(4-benzyl-2-vinyl-1-piperazinyl)carbonyl]-3-butenylcarbamate

HRID 1060615노트

반응식

HRID 1060615 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH:25]([CH:29]=[CH2:30])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC>C(Cl)Cl>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH:14]=[CH2:15])=[O:12])[CH:25]([CH:29]=[CH2:30])[CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acidHCID 146122431-Benzyl-3-vinylpiperazine

생성물 1

HCID 10200953tert-butyl (1S)-1-[(4-benzyl-2-vinyl-1-piperazinyl)carbonyl]-3-butenylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2S)-2-[(tert-butoxycarbonyl)amino]-4-pentenoic acid (466 mg, 2.17 mmol) and 1-benzyl-3-vinylpiperazine (436 mg, 2.17 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiinide hydrochloride (HOBT, 622 mg, 3.26 mmol) were combined with anhydrous CH2Cl2 (10 mL) at room temperature. Et3N (0.74 mL, 5.43 mmol) was added in one portion. The resulted solution was maintained at room temperature for 18 h at which time it was concentrated in vacuo to a volume of approximately 5 mL. Then the solution was purified by silica gel chromatography (SGC) eluting with 2:1 hex-EtOAc. The title compound (a pair of diastereomers) was obtained (171 mg, 20%) as a pale-yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.31 (s, 5H), 5.99-5.82 (m, 1H), 5.81-5.65 (m, 1H), 5.50-5.00 (m, 6H), 4.75-4.23 (m, 2H), 3.70-3.37 (m, 3H), 3.11-2.79 (m, 2H), 2.59-2.00 (m, 4H), 1.42 (s, 9H) ppm. MS (CI) 400.6 (M+H).

후처리

  1. concentrationwas concentrated in vacuo to a volume of approximately 5 mL
  2. customThen the solution was purified by silica gel chromatography (SGC)
  3. washeluting with 2:1 hex-EtOAc

출처 및 근거

ORD 기록
ord-1da030e96ed8440780d110745342b578
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525044B2

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