Ammonium Hydroxide → N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide

HRID 1845720

반응식

HRID 1845720 반응식
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:8][CH2:9][CH2:10][C:11](ON2C(=O)CCC2=O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][OH:45].[OH-].[NH4+]>ClCCl>[OH:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][NH:33][C:11](=[O:12])[CH2:10][CH2:9][S:8][C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 160103Ethanol, 2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-HCID 179354262,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoate

생성물 1

HCID 68927996N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide수율 82.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Succinimido 3-(triphenylmethylthio)propanoate (4.06 mg, 9.12 mmol) was added to a 0° C. solution of 2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethanol (C. Bertozzi and M. Bednarski, J. Org. Chem. 1991, 56, 4326-4329) (9.12 mmol) in dichloromethane (20 mL). The solution was stirred at room temperature for 2 days and concentrated ammonium hydroxide (1 mL) was added. After 20 minutes, the mixture was filtered and the filtrate was subjected to an extractive workup. The organic layer were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by HPFC on silica gel (gradient elution with 2-19% CMA in chloroform) to provide 3.95 g of N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide as a colorless oil.

후처리

  1. waitAfter 20 minutes
  2. filtrationthe mixture was filtered
  3. dry with materialThe organic layer were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by HPFC on silica gel (gradient elution with 2-19% CMA in chloroform)

출처 및 근거

ORD 기록
ord-2dd8f0e9717841589cc67d31e5e128d2
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951528B2

연결된 노트

불러오는 중…