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

HRID 1794962ノート

反応式

HRID 1794962 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ffc349b066f24badb3f7d47f84bce57d
出典データセット
uspto-grants-2006_04
特許番号
US07022851B2

反応ノート

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