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1-Hydroxybenzotriazole → (S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

HRID 1379965
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HRID 1379965 반응식
[C:1]([O:5][C:6]([N:8]([CH2:20][CH:21]=[CH2:22])[C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:24][N:25](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.CN.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)(=O)C>[CH3:24][NH:25][C:10](=[O:11])[C@@H:9]([N:8]([CH2:20][CH:21]=[CH2:22])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 12944586HCID 12944586, 화합물

생성물 1

HCID 86750266(S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Combine (S)-2-[N-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionic acid (0.7 g, 2.29 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.50 g, 2.52 mmol), 1-hydroxybenzotriazole (0.38 g, 2.52 mmol), methylamine hydrochloride (0.17 g, 2.52 mmol) and diisopropylethylamine (0.59 mL, 2.52 mmol) in dichloromethane (23 mL) and stir for 18 hours. Dilute with ethyl acetate and extract with 1M hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. Dry the separated organic layer over MgSO4, filter and evaporate in vacuo. Chromatograph on silica gel eluting sequentially with 5% methanol/dichloromethane and 10% methanol/dichloromethane to give the title compound: TLC Rf =0.44 (silica gel, 30% ethyl acetate/hexane).

후처리

  1. extractionextract with 1M hydrochloric acid
  2. dry with materialDry the separated organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-d88ec3d4b0514c11a2c6ef329cf38e08
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05672602

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