Dipropargylamine → 2,4-Bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide

HRID 1486507ノート

反応式

HRID 1486507 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19]C2C=CC=CC=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.ON1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2N=N1.[CH2:51]([NH:54][CH2:55][C:56]#[CH:57])[C:52]#[CH:53]>ClCCl>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([N:54]([CH2:55][C:56]#[CH:57])[CH2:51][C:52]#[CH:53])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 23350DipropargylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

生成物 1

HCID 581575202,4-Bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (Example 1 Step 6) (1 equivalent) in dichloromethane (10 ml) was treated successively with N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.2 equivalents), 1-hydroxybenzotriazole (1.2 equivalents) and dipropargylamine (1.5 equivalents) and the mixture was stirred at room temperature overnight. The mixture was washed successively with 2M hydrochloric acid and 2M sodium hydroxide, the organic layer was separated and the solvent removed in vacuo to afford the product which was either obtained pure or was purified by column chromatography on silica (eluting with mixtures of ethyl acetate in petroleum ether or methanol in ethyl acetate as appropriate). MS: [M+H]+ 450

後処理

  1. washThe mixture was washed successively with 2M hydrochloric acid and 2M sodium hydroxide
  2. customthe organic layer was separated
  3. customthe solvent removed in vacuo
  4. customto afford the product which
  5. customwas purified by column chromatography on silica (eluting with mixtures of ethyl acetate in petroleum ether or methanol in ethyl acetate as appropriate)

出典と根拠

ORDレコード
ord-1059e1c028864b8fb8be3f5b41a107dc
出典データセット
uspto-grants-2016_08
特許番号
US09428439B2

反応ノート

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