Triphenylphosphine → HCID 69252373、化合物

HRID 902700ノート

反応式

HRID 902700 の反応式
[Cl:1][C:2]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][OH:9].[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47](O)[CH:46]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]3[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:30])[F:31])[C:2]=3[Cl:1])[CH2:10][CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:46]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 18669061tert-Butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

生成物 1

HCID 69252373HCID 69252373、化合物収率 84%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a stirring solution of 3-[(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propan-1-ol (448 mg, 1.0 mmol) in toluene (30 mL) was added 4-(3-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (419 mg, 1.50 mmol). Polymer bound triphenylphosphine (500 mg, 1.50 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture stirred for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (303 mg, 1.50 mmol) was added in a dropwise fashion. After stirring at room temperature overnight, the crude reaction mixture was filtered and the solid washed with toluene. Concentration of the filtrate in vacuo followed by purification by flash silica gel chromatography (silica gel 60, EM science; 15% EtOAc:hexane) afforded title compound as an oil (0.59 g, 84%). MS(ES) m/e 708.4 (M+).

後処理

  1. additionwas then added
  2. stirringAfter stirring at room temperature overnight
  3. customthe crude reaction mixture
  4. filtrationwas filtered
  5. washthe solid washed with toluene
  6. customConcentration of the filtrate in vacuo followed by purification by flash silica gel chromatography (silica gel 60, EM science; 15% EtOAc:hexane)

出典と根拠

ORDレコード
ord-66198db799b84ca5a66e43faee1ac1b2
出典データセット
uspto-grants-2008_04
特許番号
US07365085B2

反応ノート

読み込み中…