홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Propionitrile → (2S,4R)-4-(4-Bromo-2-chloro-phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 69531
노트
인쇄 미리보기

반응식

HRID 69531 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([Cl:9])[CH:3]=1.[CH2:10]([N:12](CC)[CH2:13][CH3:14])[CH3:11].[C:17]([O-:20])([O-:19])=O.[Na+].[Na+].[CH:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[C:30](#N)CC>>[CH3:30][O:19][C:17]([C@@H:13]1[CH2:14][C@@H:11]([S:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[Cl:9])[CH2:10][N:12]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 7854PropionitrileHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 61207tert-Butyl FormateHCID 199152914-Bromo-2-chlorobenzene-1-thiol

생성물 1

HCID 89736507(2S,4R)-4-(4-Bromo-2-chloro-phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

실험 절차

CAS #1252633-25-2 (5.3 g, 12.3 mmol, Eq: 1.00) was dissolved in propionitrile (40 ml) and 4-bromo-2-chlorobenzenethiol (3.3 g, 14.8 mmol, Eq: 1.20) was added. Now triethyl amine (2.49 g, 3.43 ml, 24.6 mmol, Eq: 2.00) was added. The reaction mixture was stirred at reflux over night. The reaction mixture was poured into 100 ml 10% Na2CO3 and extracted with EtOAc (2×100 mL). The organic layer was extracted with 100 ml 0.1N HCl, dried over Na2SO4, filtered and evaporated. The crude material was purified by flash chromatography (silica gel, 120 g, 0% to 30% AcOEt in heptane in 30 min) to yield a colorless oil (4.72 g; 85%). m/z=352.1 [M+H-Boc]+.

후처리

  1. temperatureat reflux over night
  2. extractionextracted with EtOAc (2×100 mL)
  3. extractionThe organic layer was extracted with 100 ml 0.1N HCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash chromatography (silica gel, 120 g, 0% to 30% AcOEt in heptane in 30 min)
  8. customto yield a colorless oil (4.72 g; 85%)

출처 및 근거

ORD 기록
ord-3d65d10b676b46029e1ab66c58c20ce0
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822505B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트