1,1'-Carbonyldiimidazole → 4-(12-tert-Butoxycarbonylaminododecanoyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 2420753ノート

反応式

HRID 2420753 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl>[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][N:45]([C:20](=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:36])[CH3:37]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 4428132Boc-12-Ado-OH

生成物 1

HCID 672154104-(12-tert-Butoxycarbonylaminododecanoyl)piperazine-1-carboxylic acid tert-butyl ester収率 94.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 12-tert-butoxycarbonylaminododecanoic acid (3) (320 mg, 1.01 mmol) and 1,1′-carbonyldiimidazole (181 mg, 1.12 mmol) in anhydrous CH2Cl2 (10 mL) was stirred at room temperature for 2 hours. Then N-tert-butoxycarbonylpiperazine (227.0 mg, 1.22 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 66 hours. After this time, the solvent was removed by rotary evaporation and the resulting residue was purified with Biotage silica gel column chromatography, eluting with 5% to 36% ethyl acetate/hexanes, to afford the desired amide 10 (462.0 mg, 94%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.25 (m, 14H), 1.42 (s, 9H), 1.47 (s, 9H), 1.62 (m, 2H), 2.30 (t, 2H), 3.10 (m, 2H), 3.42 (m, 6H), 3.60 (m, 2H), 4.49 (br, 1H). m/z (ESI) 484 [C26H49N3O5+H]+.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 66 hours
  2. customAfter this time, the solvent was removed by rotary evaporation
  3. customthe resulting residue was purified with Biotage silica gel column chromatography
  4. washeluting with 5% to 36% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-e7b5f48ba0d94ec29c9ccae3119f0dfc
出典データセット
uspto-grants-2011_06
特許番号
US07956059B2

反応ノート

読み込み中…