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Propylamine → N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide

HRID 1581993
ノート
印刷プレビュー

反応式

HRID 1581993 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=O)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][CH3:23].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:21]([NH:24][C:18]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17]2)=[O:20])[CH2:22][CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 227195982-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylic acid

生成物 1

HCID 22719592N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide収率 63.6%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

2-(tert-butoxycarbonylamino)-5-carboxyindan (30 mg, 0.11 mmol) synthesized in Preparation Example 4, n-propylamine (20 μl, 0.24 mmol), triethylamine (0.20 ml, 1.4 mmol), propanephosphonic acid anhydride (0;3 ml) (see Japanese Unexamined Patent Publication (Kokai) No. 55-100346), and dimethylaminopyridine (a catalytic amount) in methylene chloride (0.25 ml) were stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and then washed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine, an aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 3:7) to obtain N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide (22 mg, 0.070 mmol) having the following-physical properties:

後処理

  1. washwashed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine
  2. dry with materialan aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 3:7)

出典と根拠

ORDレコード
ord-7b58f28862594ab2a1d6a1cbeef7b57d
出典データセット
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06734180B1

反応ノート

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