Dimethylformamide → HCID 10602177、化合物

HRID 1653683

反応式

HRID 1653683 の反応式
[CH3:1]N(C=O)C.[NH2:6][C:7]1[N:8]=[C:9]([NH2:27])[C:10]2[C:15]([CH2:16][CH2:17][C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)=[CH:14][NH:13][C:11]=2[N:12]=1.[C:28]([O:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][C@@H:39]([C:41]([OH:43])=[O:42])[NH2:40])=[O:34])([CH3:31])([CH3:30])[CH3:29].P(C#N)(OCC)(OCC)=O>C(N(CC)CC)C>[NH2:6][C:7]1[N:8]=[C:9]([NH2:27])[C:10]2[C:15]([CH2:16][CH2:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:40][C@H:39]([C:41]([O:43][CH3:1])=[O:42])[CH2:38][CH2:37][CH2:36][NH:35][C:33]([O:32][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:34])=[O:23])=[CH:20][CH:19]=3)=[CH:14][NH:13][C:11]=2[N:12]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acidHCID 10447331HCID 10447331、化合物

生成物 1

HCID 10602177HCID 10602177、化合物収率 85%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a DMF solution of 4-[2-(2,4-diamino-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (1.52 g) and methyl ester of N(δ)-t-butyloxycarbonyl-L-ornithine (1.3 g) was added diethyl cyanophosphate (1.4 g). The mixture was stirred for one hour at room temperature in the presence of triethylamine (3.0 g). The reaction mixture was concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel (carrier: 30 g; chloroform:ethanol containing 1% ammonium=20:1-15:1) to afford methyl N(α)-[4-[2-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-N-(δ)-(t-butyloxycarbonyl)-L-ornithinate (2.30 g; yield 85%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe concentrate was purified by column chromatography on silica gel (carrier: 30 g; chloroform:ethanol containing 1% ammonium=20:1-15:1)

出典と根拠

ORDレコード
ord-6c87443a3ce54b5fa4461fbfe227b526
出典データセット
uspto-grants-1995_04
特許番号
US05403843

関連ノート

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