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

HRID 2420753노트

반응식

HRID 2420753 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-e7b5f48ba0d94ec29c9ccae3119f0dfc
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956059B2

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