Potassium Carbonate → HCID 67682555、化合物

HRID 1751650ノート

反応式

HRID 1751650 の反応式
[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]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 59610197tert-butyl N-[2-(4-bromophenyl)-2-oxoethyl]carbamateHCID 67682938HCID 67682938、化合物

生成物 1

HCID 67682555HCID 67682555、化合物収率 58.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b9c50ccc9dbc4772bbd576bb84a6b8f5
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

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