1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-Boc-S-trityl-cysteinyl-3-aminomethyl-3'-tert-butoxycarbonylbiphenyl

HRID 849304노트

반응식

HRID 849304 반응식
N([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)=[N+]=[N-].[C:23]([NH:30][C@H:31]([C:53]([OH:55])=O)[CH2:32][S:33][C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C[CH2:57][N:58]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CO.[Pd]>[C:23]([NH:30][C@H:31]([C:53]([C:5]1[C:4]([CH2:57][NH2:58])=[CH:9][CH:8]=[CH:7][C:6]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:11]=1)=[O:55])[CH2:32][S:33][C:34]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24]

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11167161N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 195916263-Azido-3'-tert-butoxycarbonylbiphenyl

생성물 1

HCID 18392929N-Boc-S-trityl-cysteinyl-3-aminomethyl-3'-tert-butoxycarbonylbiphenyl수율 44%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

Compound 20 (0.75 g, 2.43 mmol) was dissolved in 30 mL of methanol. A catalytic amount of 5% palladium on barium sulfate (0.30 g) was added. The mixture was hydrogenated at 1 atm for 5 hr. The catalyst was removed by filtration and the methanol was evaporated. This residue was dissolved in 40 mL of methylene chloride. N-Boc-S-trityl cysteine (1.12 g, 2.43 mmol) was added at 0° C. followed by EDCI (1 eq) and HOBT (1 eq). The mixture was stirred for 24 hr. After workup and evaporation of solvents, the residue was purified by flash column chromatography (hexane:ethyl acetate=3.2:1) to give 21 (570 mg, 44%). m.p. 84-86° C. 1H NMR (CDCl3) δ 8.17 (s, 1H), 7.95 (d, 7.7 Hz, 1H), 7.70 (d, 7.7 Hz, 1H), 7.50-7.30 (m, 9H), 7.30-7.10 (m, 11H), 6.44 (br, 1H), 4.86 (br, 1H), 4.45 (d, 4.0 Hz, 2H, CH2Ph), 3.87 (br, 1H, Cys α H), 2.75 (dd, 7.2 and 12.8 Hz, 1H, CH2S), 2.55 (dd, 5.3 and 12.8 Hz, 1H, CH2S), 1.62 (s, 9H), 1.36 (s, 9H). Anal. (C45H48N2O5S) C, H, N, S.

후처리

  1. customThe catalyst was removed by filtration
  2. customthe methanol was evaporated
  3. dissolutionThis residue was dissolved in 40 mL of methylene chloride
  4. customAfter workup and evaporation of solvents
  5. customthe residue was purified by flash column chromatography (hexane:ethyl acetate=3.2:1)

출처 및 근거

ORD 기록
ord-db739182121b4640bc55a3512708fb46
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011175

반응 노트

불러오는 중…