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Dicyclohexylcarbodiimide → Ethyl 4-(2-(12-(Isopropylthio)dodecanoylamino)-phenoxy)-butyrate

HRID 1290703
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인쇄 미리보기

반응식

HRID 1290703 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:17]([S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](O)=[O:33])([CH3:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:17]([S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:33])([CH3:19])[CH3:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 11816929Ethyl 4-(2-aminophenoxy)butanoateHCID 1879628012-[(Propan-2-yl)sulfanyl]dodecanoic acid

생성물 1

HCID 18796054Ethyl 4-(2-(12-(Isopropylthio)dodecanoylamino)-phenoxy)-butyrate수율 45.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매
3회

실험 절차

To a solution of (4) (0.25 g, 1.14 mM) and (6) (0.274 g, 1.0 mM) in dry methylene chloride (10 mL) at room temperature was added 4-dimethylaminopyridine (0.122 g, 1.0 mM) followed within one minute by a solution of N,N'-dicyclohexylcarbodiimide (0.22 g, 1.06 mM) in methylene chloride (1 mL), 3×1 mL rinses with methylene chloride. After 2 days, the filtered mixture was concentrated in vacuo and the residue flash chromatographed on silica gel using 15-20% ethyl acetate in hexane as eluant to give product 7 (0.22 g) as an oil that solidified readily in a short time.

후처리

  1. concentrationthe filtered mixture was concentrated in vacuo
  2. customthe residue flash chromatographed on silica gel using 15-20% ethyl acetate in hexane as eluant

출처 및 근거

ORD 기록
ord-8af82da3beeb47398ca5c5197c3b2d6a
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05753641

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