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

Formic Acid → 2-[4-(tert-Butoxycarbonyl)benzyl]-4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]butanoic acid

HRID 1920590
노트
인쇄 미리보기

반응식

HRID 1920590 반응식
C(N(CC)CC)C.C(O)=O.[C:11]([O:15][C:16]([C:18]1[CH:48]=[CH:47][C:21]([CH2:22][C:23]([CH2:36][CH2:37][C:38]2([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:40][CH2:39]2)(C(OCC=C)=O)[C:24]([O:26]CC=C)=[O:25])=[CH:20][CH:19]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:15][C:16]([C:18]1[CH:48]=[CH:47][C:21]([CH2:22][CH:23]([CH2:36][CH2:37][C:38]2([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:40][CH2:39]2)[C:24]([OH:26])=[O:25])=[CH:20][CH:19]=1)=[O:17])([CH3:13])([CH3:12])[CH3:14]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57965749Diallyl [4-(tert-butoxycarbonyl)benzyl]{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}malonate

생성물 1

HCID 579657452-[4-(tert-Butoxycarbonyl)benzyl]-4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]butanoic acid

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 312751,4-Dioxane용매2회

반응 조건

온도
100 °C

실험 절차

At room temperature, a solution of 7.42 ml (53.56 mmol) of triethylamine and 1.53 ml (40 mmol) of formic acid in 25 ml of dioxane is added to a solution of 8.58 g (16.2 mmol) of diallyl [4-(tert-butoxycarbonyl)benzyl]{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}malonate, 298 mg (1.14 mmol) of triphenylphosphine and 73 mg (0.33 mmol) of palladium acetate in 75 ml of dioxane. The reaction mixture is then stirred at 100° C. for 2 hours. After complete conversion, the reaction solution is cooled and the solvent is removed under reduced pressure. The residue is then taken up in ethyl acetate and water and acidified with 1 N hydrochloric acid (pH 4-5), and the organic phase is separated off. The aqueous phase is extracted three more times with ethyl acetate, and the organic phases are then combined, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solution is concentrated under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (700 g; mobile phase: petroleum ether/ethyl acetate 1:1). This gives 4.9 g (74.6% of theory) of a colorless solid.

후처리

  1. temperatureAfter complete conversion, the reaction solution is cooled
  2. customthe solvent is removed under reduced pressure
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted three more times with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solution is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d81ed0b128474404a0baf6cf7893e6c4
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08168821B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트