Water → HCID 67454416, 화합물

HRID 1713260노트

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HRID 1713260 반응식
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[CH2:17]([O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].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.CN(C)C=O>[CH2:17]([O:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343133-Benzyloxy-phenylboronic acidHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamate

생성물 1

HCID 67454416HCID 67454416, 화합물수율 78.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a mixture of tert-butyl N-(4-bromobenzyl)carbamate (5.00 g), 3-benzyloxyphenylboronic acid (4.38 g), sodium carbonate (3.70 g), water (14 mL) and N,N-dimethylformamide (70 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.01 g), and the resulting mixture was stirred at 80° C. for 14 hours. The reaction mixture was cooled to room temperature and the insoluble material was filtered out. The filtrate was partitioned between ethyl acetate (110 mL) and water (50 mL). The organic layer was washed successively with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=6/1) to give the title compound (5.32 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble material was filtered out
  3. customThe filtrate was partitioned between ethyl acetate (110 mL) and water (50 mL)
  4. washThe organic layer was washed successively with water (50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=6/1)

출처 및 근거

ORD 기록
ord-79cc25f734514d07bee7114994ac9861
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795236B2

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