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Pyridine → 1-Cyano-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane

HRID 987128
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HRID 987128 반응식
[C:1]([CH:4]([O:29][CH2:30][CH3:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)(=O)[NH2:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[C:1]([CH:4]([O:29][CH2:30][CH3:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 229884671-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane

생성물 1

HCID 229884631-Cyano-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane수율 77.9%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

1-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane(0.63 g, 1.47 mmole) was dissolved in dioxane (20 ml) and pyridine (0.35 g, 4.41 mmole) was added. The mixture was placed in a ultrasonic bath for 5 minutes, then trifluoroacetic acid anhydride (0.37 g, 1.76 mmole) was added. After stirring at room temperature for 16 hours it was checked using HPLC that all the starting material was consumed. Sodium carbonate solution was added and extracted three times with dichloromethane. The organic phase was dried with magnesium sulfate and evaporated. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm) using acetronitrile (70-80%) in ammonium acetate buffer (pH 7) as mobil phase gave 0.47 g (75% yield) of the desired product.

후처리

  1. customwas consumed
  2. additionSodium carbonate solution was added
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customevaporated
  6. customPurification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm)

출처 및 근거

ORD 기록
ord-cd42a5e9a1f04f6985bc90d9cc11bced
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06630509B2

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