1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-{[(1H-1,2,4-triazol-1-ylacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022814

반응식

HRID 1022814 반응식
[NH2:1][CH2:2][CH:3]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH:4]1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:46]1([CH2:51][C:52](O)=[O:53])[CH:50]=[N:49][CH:48]=[N:47]1.C(=O)([O-])O.[Na+]>CN(C=O)C.C(N(CC)CC)C>[Cl:24][C:19]1[CH:18]=[C:17]([CH:4]2[CH:3]([CH2:2][NH:1][C:52](=[O:53])[CH2:51][N:46]3[CH:50]=[N:49][CH:48]=[N:47]3)[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 18101801,2,4-Triazole-1-acetic acidHCID 66975190tert-butyl (6RS,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

생성물 1

HCID 66976357tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-{[(1H-1,2,4-triazol-1-ylacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate수율 73.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of tert-butyl (6SR,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) in DMF (5 mL) were added WSC (100 mg), HOBt (90 mg), triethylamine (0.10 mL) and 2-(1H-1,2,4-triazol-1-yl)acetic acid (74 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (190 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1f6867cb3bf64e0ea833723f471d5ac2
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722662B2

연결된 노트

불러오는 중…