Potassium Carbonate → HCID 67682555, 화합물

HRID 1751650노트

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HRID 1751650 반응식
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C@H:6]([C:19]2[NH:20][C:21]([C:24]3[CH:29]=[CH:28][C:27](B4OC(C)(C)C(C)(C)O4)=[CH:26][CH:25]=3)=[CH:22][N:23]=2)[CH2:5]1.Br[C:40]1[CH:45]=[CH:44][C:43]([C:46](=[O:56])[CH2:47][NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:42][CH:41]=1.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>[C:51]([O:50][C:49]([NH:48][CH2:47][C:46]([C:43]1[CH:42]=[CH:41][C:40]([C:27]2[CH:28]=[CH:29][C:24]([C:21]3[NH:20][C:19]([C@@H:6]4[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[CH2:8][N:7]4[C:9]([O:11][CH2:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[O:10])=[N:23][CH:22]=3)=[CH:25][CH:26]=2)=[CH:45][CH:44]=1)=[O:56])=[O:55])([CH3:54])([CH3:52])[CH3:53]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 59610197tert-butyl N-[2-(4-bromophenyl)-2-oxoethyl]carbamateHCID 67682938HCID 67682938, 화합물

생성물 1

HCID 67682555HCID 67682555, 화합물수율 58.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

(2S,4S)-benzyl 4-(methoxymethyl)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (500 mg, 0.97 mmol), tert-butyl 2-(4-bromophenyl)-2-oxoethylcarbamate (364 mg, 1.16 mmol), Pd(PPh3)4 (112 mg, 0.097 mmol), and K2CO3 (2M in H2O, 1.6 mL, 3.2 mmoL) were combined in DME (10 mL). The mixture was degassed with bubbling N2 for 10 min the heated to 85° C. for 18 h. After cooling, the reaction mixture was diluted with EtOAc, and washed successively with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc) to afford product (357 mg, 56%).

후처리

  1. customThe mixture was degassed with bubbling N2 for 10 min the
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed successively with saturated aqueous NaHCO3 and brine
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-b9c50ccc9dbc4772bbd576bb84a6b8f5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

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