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Triethylamine → 4-[[(N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl)amino]methyl]-1-(4-chlorobenzyl)piperidine

HRID 133608
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HRID 133608 반응식
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][C:16]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:17]=1[C:18]([OH:20])=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[Cl:50][C:51]1[CH:69]=[CH:68][C:54]([CH2:55][N:56]2[CH2:61][CH2:60][CH:59]([CH2:62][NH:63][C:64](=[O:67])[CH2:65][NH2:66])[CH2:58][CH2:57]2)=[CH:53][CH:52]=1.[OH-].[Na+]>ClCCl>[C:8]([O:12][C:13]([NH:15][C:16]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:17]=1[C:18]([NH:66][CH2:65][C:64]([NH:63][CH2:62][CH:59]1[CH2:60][CH2:61][N:56]([CH2:55][C:54]2[CH:68]=[CH:69][C:51]([Cl:50])=[CH:52][CH:53]=2)[CH2:57][CH2:58]1)=[O:67])=[O:20])=[O:14])([CH3:9])([CH3:10])[CH3:11]
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참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 184261442-((Tert-butoxycarbonyl)amino)-4,5-difluorobenzoic acidHCID 184261541-(4-Chlorobenzyl)-4-[(glycylamino)methyl]piperidine dihydrochloride

생성물 1

HCID 184261994-[[(N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl)amino]methyl]-1-(4-chlorobenzyl)piperidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (1.1 mL, 8 mmol), 2-(tert-butoxycarbonylamino)-4,5-difluorobenzoic acid (607 mg, 2.2 mmol), EDCI (422 mg, 2.2 mmol) and HOBt (337 mg, 2.2 mmol) were added to a dichloromethane (20 mL) solution of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine dihydrochloride (738 mg, 2 mmol), and the resulting mixture was stirred at room temperature for 14 hours. A 0.6 M aqueous solution of NaOH (50 mL) was then added to the mixture, and the obtained mixture was extracted with dichloromethane (3 times). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to thereby provide 4-[[(N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl) glycyl)amino]methyl]-1-(4-chlorobenzyl)piperidine (1.01 g, 92%). ESI/MS m/e 551.3 (M++H, C27H33ClF2N4O4).

후처리

  1. extractionthe obtained mixture was extracted with dichloromethane (3 times)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to thereby provide 4-[[(N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl) glycyl)amino]methyl]-1-(4-chlorobenzyl)piperidine (1.01 g, 92%)

출처 및 근거

ORD 기록
ord-d28599fe984941de9bac9910aa2ad906
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07390830B1

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