Triethylamine → benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-cyanobenzoylamino)butanoate

HRID 747768노트

반응식

HRID 747768 반응식
[Cl-].[CH2:2]([O:9][C:10]([CH2:12][C@@H:13]([NH3+:25])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:17]=1[I:24])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)#[N:27].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[C:22]([C:20]1[CH:19]=[CH:18][C:17]([I:24])=[C:16]([CH:21]=1)[O:15][CH2:14][C@H:13]([NH:25][C:32](=[O:33])[C:31]1[CH:35]=[CH:36][C:28]([C:26]#[N:27])=[CH:29][CH:30]=1)[CH2:12][C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:11])#[N:23]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760714(1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride

생성물 1

HCID 54164296benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-cyanobenzoylamino)butanoate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

4.73 g (10 mmol) of (1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride, 2.9 g (20 mmol) of 4-cyanobenzoic acid, 3.0 g (22 mmol) of 1-hydroxybenzotriazole and 6.1 ml (44 mmol) of triethylamine were dissolved in 50 ml of dichloromethane. 4.2 g (22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to the solution under cooling with ice, and they were stirred for 10 minutes and then at room temperature for one hour. Water is added to the reaction mixture to terminate the reaction. The mixture was treated with dichloromethane as the extractant in an ordinary manner to obtain the crude product, which was purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=3:1) to obtain the title compound.

후처리

  1. temperatureunder cooling with ice, and they
  2. waitat room temperature for one hour
  3. customto terminate
  4. customthe reaction
  5. customto obtain the crude product, which
  6. customwas purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-0ce0e02527c842c7999849f0faed2d91
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396844B1

반응 노트

불러오는 중…