Potassium Carbonate → HCID 90289950, 화합물

HRID 1471629노트

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HRID 1471629 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:30][C:31]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10](=[O:11])[C@@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:30]=[CH2:31])[CH:3]=2)=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 90289952HCID 90289952, 화합물

생성물 1

HCID 90289950HCID 90289950, 화합물수율 98%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A suspension of (S)-tert-butyl 3-(3-bromophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (6.3 g, 13.6 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.3 g, 20.4 mmol), potassium carbonate (54 ml, 0.4 M) and tetrakis(triphenylphosphine)palladium(0) (0.79 g, 0.68 mmol) in 50 ml of DME, was heated at reflux overnight. The suspension was cooled and filtered through celite. The filtrate was washed with brine and filtered through celite. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (15-35% EtOAc/hexanes) to provide the desired product (5.47 g, 13.33 mmol), 94%. MS (m/z) 411 [M+H]+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe suspension was cooled
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with brine
  6. filtrationfiltered through celite
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe crude product was introduced to a silica gel loading column
  11. custompurified by column chromatography (15-35% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-94faa4faca6846b7ab3e7ee0efbfd074
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012441B2

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