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

HRID 1024502노트

반응식

HRID 1024502 반응식
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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b1bd13d23f3648bca528b646e0b3f834
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722896B2

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