2-Methyl-2-butene → 2-benzyl-4-(4-carboxyphenyl)-6-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750247ノート

反応式

HRID 750247 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4].P([O-])(O)(O)=[O:33].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>O.C(O)CCC.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:33])=[O:22])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4]

参加物

8

反応物 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 865995582-benzyl-6-chloro-4-(4-formylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

生成物 1

HCID 691564702-benzyl-4-(4-carboxyphenyl)-6-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 34.2%

試薬・触媒・溶媒 3

HCID 2631-Butanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 2-benzyl-6-chloro-4-(4-formylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (93 mg), sodium dihydrogenphosphate (26 mg), 2-methyl-2-butene (100 μl), THF (2.0 ml), butanol (1.0 ml) and water (2.0 ml) was added sodium chlorite (73 mg) at 0° C. with stirring, and the mixture was stirred for 1 hr. The solvent was removed and the residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (33 mg) as a colorless powder.

後処理

  1. stirringthe mixture was stirred for 1 hr
  2. customThe solvent was removed
  3. customthe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-e50b868c3f1d436b886a8eefdc5dc53a
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

読み込み中…