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

Triethylamine → Biphenyl-4-carboxylic acid (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide

HRID 2224738
노트
인쇄 미리보기

반응식

HRID 2224738 반응식
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:20])[C:6](=[N:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C@@H:14]([OH:19])[C@@H:15]2[NH-:18])=[CH:11][CH:10]=1)[CH3:7].C(OC(=O)N)(C)(C)C.C(N(CC)CC)C.O=C1CCC(=O)N1[O:43][C:44]([C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:48][CH:47]=1)=O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:20])[C:6](=[N:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C@@H:14]([OH:19])[C@@H:15]2[NH:18][C:44]([C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[CH:48][CH:47]=2)=[O:43])=[CH:11][CH:10]=1)[CH3:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 6847362,5-Dioxopyrrolidin-1-yl [1,1'-biphenyl]-4-carboxylateHCID 86607037carbamic acid tert-butyl ester (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide

생성물 1

HCID 9804160Biphenyl-4-carboxylic acid (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide수율 50.9%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 6422Trifluoroacetic acid용매

실험 절차

Dissolve carbamic acid tert-butyl ester (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide (153.6 mg, 0.407 mmol) in excess TFA at 0° C. and allow to stir for 1 hour. Remove the solvent in vacuo. Dissolve the residue in 10 mL methylene chloride and add triethylamine (411.8 mg, 4.07 mmol) and biphenyl-4-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester (118.3 mg, 0.400 mmol). Allow the reaction mixture to stir for 21 hours. Dilute the reaction mixture with methylene chloride and wash it with saturated aqueous sodium hydrogen carbonate (1×) and brine (1×). Dry the organic layer with magnesium sulfate. Filter and remove the solvent in vacuo to give 162.1 mg of crude product. Purify via Biotage chromatography (30% MeOH/EtOAc) to afford 93.1 mg of the titled product as an oil (50% yield). MS (ES): m/z 458.3(M+H).

후처리

  1. customRemove the solvent in vacuo
  2. dissolutionDissolve the residue in 10 mL methylene chloride
  3. stirringto stir for 21 hours
  4. washwash it with saturated aqueous sodium hydrogen carbonate (1×) and brine (1×)
  5. dry with materialDry the organic layer with magnesium sulfate
  6. filtrationFilter
  7. customremove the solvent in vacuo
  8. customto give 162.1 mg of crude product
  9. customPurify via Biotage chromatography (30% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-593ec59d33854cd781be148627bb5bca
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378447B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트