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

HRID 241829노트

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HRID 241829 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-67924166b19a4afabc46ba53151dc276
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653084B2

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