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

HRID 1060615ノート

反応式

HRID 1060615 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-1da030e96ed8440780d110745342b578
出典データセット
uspto-grants-2003_02
特許番号
US06525044B2

反応ノート

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