Potassium Phosphate, Tribasic → (r/s)-3-(Tert-butoxycarbonylamino)-1-(4-cyclopropyl-5-isoquinolinesulfonyl)-pyrrolidine

HRID 1436028ノート

反応式

HRID 1436028 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:28]1(B(O)O)[CH2:30][CH2:29]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].F[B-](F)(F)F.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([CH:28]4[CH2:30][CH2:29]4)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 11710396Tricyclohexylphosphonium TetrafluoroborateHCID 67242856(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

生成物 1

HCID 67243197(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-cyclopropyl-5-isoquinolinesulfonyl)-pyrrolidine収率 29%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A suspension of Intermediate 1 (200 mg) obtained in Example 1, Step A, cyclopropylboronic acid (57 mg, Aldrich), anhydrous potassium phosphate (372 mg, Aldrich), and tricyclohexylphosphonium tetrafluoroborate (33 mg, Aldrich) in toluene (2 ml) is added with palladium acetate (10 mg, Wako Pure Chemical Industries), and the mixture is stirred at 80° C. with heating for 14 hours under a nitrogen gas atmosphere. The reaction mixture is cooled to room temperature, and then added with ethyl acetate (5 ml), and the insoluble matters are removed by filtration through Celite. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (53 mg (predictive yield)).

後処理

  1. temperaturewith heating for 14 hours under a nitrogen gas atmosphere
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customthe insoluble matters are removed by filtration through Celite
  4. customThe solvent is evaporated under reduced pressure
  5. customthe residue is purified by silica gel chromatography (n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-7039711c016d46e698c16c69b7758b34
出典データセット
uspto-grants-2009_11
特許番号
US07618984B2

反応ノート

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