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Cesium carbonate → 1-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid tert-butyl ester

HRID 1629748
ノート
印刷プレビュー

反応式

HRID 1629748 の反応式
[C:1]([O:5][C:6]([CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=2[Cl:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([C@H:29]([NH2:32])[CH2:30][CH3:31])=[CH:24][C:23]=1[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C(O)(C)(C)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[C:17]([NH:32][C@@H:29]([C:25]3[CH:24]=[C:23]([CH3:33])[C:22]([Cl:21])=[C:27]([CH3:28])[CH:26]=3)[CH2:30][CH3:31])[CH:16]=[CH:15][C:14]=2[Cl:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 55278509(R)-1-(4-Chloro-3,5-dimethyl-phenyl)-propylamineHCID 583744221-(5-Bromo-2-chloro-benzyl)azetidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 673461981-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of INT 57 (250 mg, 0.693 mmol), amine INT 38 (137 mg, 0.693 mmol) and cesium carbonate (678 mg, 2.079 mmol) in toluene (4.5 mL) and tert-butanol (1.8 mL) was purged with argon for 10 minutes. Then, XPhos (66.1 mg, 0.139 mmol) and palladium acetate (15.56 mg, 0.069 mmol) were added, the vial was closed and heated at 100° C. for 3 hours. The reaction mixture was then diluted with EtOAc (35 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated.

後処理

  1. customwas purged with argon for 10 minutes
  2. customthe vial was closed
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0848c373235b465daf2e8b4a7bf06181
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08791100B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート