Diisopropylethylamine → 4-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(2-nitro-benzenesulfonyl)-piperazin-2-one

HRID 1794962노트

반응식

HRID 1794962 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[NH:13][C:14](=[O:25])[C:15]2[N:16]=[CH:17][N:18]([CH2:21][C:22]([OH:24])=O)[C:19]=2[N:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][C:40]1=[O:45])(=[O:38])=[O:37])([O-:29])=[O:28].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[NH:13][C:14](=[O:25])[C:15]2[N:16]=[CH:17][N:18]([CH2:21][C:22]([N:42]3[CH2:43][CH2:44][N:39]([S:36]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[N+:27]([O-:29])=[O:28])(=[O:38])=[O:37])[C:40](=[O:45])[CH2:41]3)=[O:24])[C:19]=2[N:20]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 688024401-(2-Nitrobenzenesulfonyl)-piperazin-2-one HCl saltHCID 1354406332-[2-(Benzyloxycarbonylamino)-6-hydroxy-purin-9-yl]acetic acid

생성물 1

HCID 1363776444-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(2-nitro-benzenesulfonyl)-piperazin-2-one수율 58%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of [2-N-(benzyloxycarbonyl)-guanin-9-yl]-acetic acid (1.48 g, 4.5 mmol), 1-(2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (1.45 g, 4.5 mmol), and PyBOP (2.81 g, 5.4 mmol) in DMF (13 mL) was added N,N-diisopropylethylamine (1.96 mL, 13 mmol) at room temperature. After stirring for additional 40 min, the reaction mixture was diluted with water (80 mL) to precipitate solid. The solid was filtered off, washed with ethyl alcohol and triturated with acetonitrile and THF to give pure product (1.56 g, 58%). 1H NMR (DMSO-d6) δ 11.47 (s, 1H), 11.38 (s, 1H), 8.40˜7.96 (m, 4H), 7.82 (s, 0.6H), 7.78 (s, 0.4H), 7.45˜7.35 (m, 5H), 5.25 (s, 2H), 5.13 (s, 1.2H), 5.04 (s, 0.8H), 4.51 (s, 0.8H), 4.26 (s, 1.2H), 4.10˜4.02 (m, 2.4H), 3.93˜3.83 (m, 1.6H).

후처리

  1. customto precipitate solid
  2. filtrationThe solid was filtered off
  3. washwashed with ethyl alcohol
  4. customtriturated with acetonitrile and THF

출처 및 근거

ORD 기록
ord-ffc349b066f24badb3f7d47f84bce57d
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022851B2

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