Triphenylphosphine → 4-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carboxylic acid methyl ester

HRID 1185558ノート

反応式

HRID 1185558 の反応式
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5].[CH2:18]([O:25][C:26](=[O:30])[C@H:27]([CH3:29])O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH3:2][O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][C@@H:27]([C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:30])[CH3:29])[C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11052238benzyl (2S)-2-hydroxypropanoateHCID 178498501HCID 178498501、化合物

生成物 1

HCID 685993014-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1.00 g 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid methyl ester hydrochloride and 0.83 g benzyl-L-lactate in 30 ml THF were added 1.81 g triphenylphosphine and 1.20 g diethylazodicarboxylate. After 2 h LCMS indicated complete conversion and water was added to the reaction mixture which was subsequently extracted with ethyl acetate. The residue obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 1.80 g.

後処理

  1. extractionwas subsequently extracted with ethyl acetate
  2. customThe residue obtained
  3. customafter evaporation of the solvent
  4. customwas purified by flash chromatography on silica using an ethyl acetate/heptane gradient

出典と根拠

ORDレコード
ord-c70cc9f1ae454041ba3df0e844b7755f
出典データセット
uspto-grants-2014_03
特許番号
US08669266B2

反応ノート

読み込み中…