Tributylphosphine → 3-{4-[1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl ester

HRID 1669330ノート

反応式

HRID 1669330 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24](O)[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:19]=1[CH3:32].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:24]([C:21]2[CH:22]=[CH:23][C:18]([Br:17])=[C:19]([CH3:32])[CH:20]=2)[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:12][CH:13]=1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 106328533-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 673450331-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol

生成物 1

HCID 673419823-{4-[1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl ester収率 63%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (805 mg, 3.61 mmol) and 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol (824 mg, 2.89 mmol) in toluene (15.0 mL) was degassed and filled with nitrogen for 3 times. Tributylphosphine (1.1 mL, 4.33 mmol) was added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (1.1 g, 4.33 mmol). The reaction mixture was allowed to warm to room temperature and stirred over night, the mixture was loaded on silica gel column. Chromatography gave the title compound (890 mg, 1.82 mmol).

後処理

  1. additionfilled with nitrogen for 3 times

出典と根拠

ORDレコード
ord-66cc52cc37704c038a0a0c6c7c1ff829
出典データセット
uspto-grants-2011_08
特許番号
US07989457B2

反応ノート

読み込み中…