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Water → HCID 57635634, 화합물

HRID 1971119
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HRID 1971119 반응식
Br[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13]([NH:15][C@@H:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH:19][CH3:20])=[O:18])=[O:14])[N:3]=1.[C:25]([Si:29]([CH3:45])([CH3:44])[O:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/B1OC(C)(C)C(C)(C)O1)([CH3:28])([CH3:27])[CH3:26].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:29]([O:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13]([NH:15][C@@H:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH:19][CH3:20])=[O:18])=[O:14])[N:3]=1)([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:44])[CH3:45]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16217344(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silaneHCID 57635118HCID 57635118, 화합물

생성물 1

HCID 57635634HCID 57635634, 화합물수율 99.7%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
160 °C

실험 절차

To a solution of compound 324 (0.10 g, 0.25 mmol) in dioxane (2 mL) was (E)-tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyloxy)silane (0.115 g, 0.50 mmol), followed by K2CO3 (0.069 g, 0.50 mmol) and water (0.40 mL). The resulting mixture was degassed with nitrogen and Pd(PPh3)4 (0.023 g, 0.02 mmol) was added. The mixture was heated in microwave reactor at 160° C. for 20 min. The mixture was diluted with EtOAc, and filtered through celite. The organic layer was concentrated, washed with water, dried over anhydrous Na2SO4 and concentrated again. The residue was purified using PL-Thiol MP SPE tube to provide compound 47A (0.126 g, 99%). LCMS (+ESI) m/z 506.4 [M+H]+.

후처리

  1. additionwas added
  2. filtrationfiltered through celite
  3. concentrationThe organic layer was concentrated
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated again
  7. customThe residue was purified

출처 및 근거

ORD 기록
ord-035613c87eb84e70936f010723deb009
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431565B2

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