Dimethylformamide → 1-(9H-fluoren-9-yl)methyl 4-tert-butyl 2-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1,4-dicarboxylate

HRID 1896103

反応式

HRID 1896103 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9]1[C:21]2[CH:20]([CH2:22][O:23][C:24]([N:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH:27]3[CH2:39][C:40](O)=[O:41])=[O:25])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.CN(C)C=O.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:40](=[O:41])[CH2:39][CH:27]1[CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31][N:26]1[C:24]([O:23][CH2:22][CH:20]1[C:21]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[C:19]1=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:25]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 119922-BromoanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27567961-Fmoc-4-Boc-Piperazine-2-acetic acid

生成物 1

HCID 582849301-(9H-fluoren-9-yl)methyl 4-tert-butyl 2-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 2-bromoaniline (3.69 g, 21.44 mmol), and 2-(1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid (10 g, 21.44 mmol) in a 1:1 solution of N,N-dimethylformamide:pyridine (100 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.27 g, 53.6 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and was subsequently washed with brine (3×) and 1 M HCl (3×). The organic solution was then concentrated onto silica gel and purified via flash chromatography (10-70% ethyl acetate/hexanes) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.43 (s, 1 H), 7.81-7.95 (m, J=7.67 Hz, 2 H), 7.53-7.75 (m, 4 H), 7.22-7.48 (m, 5 H), 7.10 (dd, J=7.21 Hz, 1 H), 4.56 (s, 1 H), 4.17-4.42 (m, 3 H), 3.61-3.98 (m, 3 H), 2.89-3.18 (m, 2 H), 2.62-2.88 (m, 2 H), 2.49-2.58 (m, 1 H), 1.32-1.50 (m, 9 H); MS (APCI+) m/z 522.2 (M-Boc+H)+.

後処理

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwas subsequently washed with brine (3×) and 1 M HCl (3×)
  4. concentrationThe organic solution was then concentrated onto silica gel
  5. custompurified via flash chromatography (10-70% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-4be111d48f754ccd8f62489f94b6f4f7
出典データセット
uspto-grants-2013_08
特許番号
US08518933B2

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