Water → (+/-)-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl-3-(phenylamino)cyclopentanecarboxamide

HRID 1024502

反応式

HRID 1024502 の反応式
Cl[C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.[C:19]1([NH:25][CH:26]2[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=O)[CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.C(N=C=NCCCN(C)C)C.O>CN(C1C=CN=CC=1)C.ClCCl>[O:8]1[C:7]2[CH:2]=[CH:3][C:4]([CH2:13][N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:31]([CH:28]3[CH2:29][CH2:30][CH:26]([NH:25][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:27]3)=[O:33])=[CH:5][C:6]=2[O:12][CH2:11][CH2:10][CH2:9]1

参加物

7

反応物 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amineHCID 57665758HCID 57665758、化合物

生成物 1

HCID 46831590(+/-)-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl-3-(phenylamino)cyclopentanecarboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

The mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (17 mg), 3-phenylaminocyclopentanecarboxylic acid (15 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (20 mg), and N,N-dimethyl-4-aminopyridine (12 mg) in 5 ml dichloromethane was stirred at room temperature overnight. After addition of water (5 mL), the mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Preparative thin layer chromatography on silica (33% ethyl acetate in hexane) gave the product as a resin: MS (m+1)=423.3; H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 1.30 (m, 4H), 1.75 (m, 2H), 1.90 (m, 1H), 1.95 (m, 1H), 2.15 (m, 1H), 2.30 (m, 1H), 2.65 (m, 2H), 3.00 (m, 1H), 4.00 (m, 2H), 4.40 (m, 2H), 4.15 (m, 4H), 5.20 (s, 1H), 6.6-6.8 (m, 3H), 7.1-7.6 (m, 5H).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (10 ml×2)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPreparative thin layer chromatography on silica (33% ethyl acetate in hexane) gave the product as a resin

出典と根拠

ORDレコード
ord-b1bd13d23f3648bca528b646e0b3f834
出典データセット
uspto-grants-2014_05
特許番号
US08722896B2

関連ノート

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