Lithium hydroxide, monohydrate → (R)-3-(2-tert-Butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1193287ノート

反応式

HRID 1193287 の反応式
O[Li].O.[C:4]([C:8]1[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=1[C:10]([NH:12][C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)=[O:11])([CH3:7])([CH3:6])[CH3:5].OS([O-])(=O)=O.[K+]>O.CO.C1COCC1>[C:4]([C:8]1[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=1[C:10]([NH:12][C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)=[O:11])([CH3:7])([CH3:5])[CH3:6]

参加物

6

反応物 3

HCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 66798706(R)-Methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

生成物 1

HCID 66798589(R)-3-(2-tert-Butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

LiOH.H2O (700 g, 17.0 mmol, 6 eq), dissolved in water (30 ml), was added dropwise to a cooled (0° C.) solution of (R)-methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-27) (1.0 g, 2.8 mmol, 1 eq) in MeOH:THF (1:1, 60 ml), and stirring was carried out for 4 h at RT. After monitoring by thin-layer chromatography, the reaction solution was reduced under reduced pressure and the residue was taken up in water (50 ml), acidified with KHSO4 solution and extracted with dichloromethane (2×100 ml). The combined organic phases were washed with sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated and dried under reduced pressure. Yield: 900 mg

後処理

  1. additionwas added dropwise to
  2. extractionextracted with dichloromethane (2×100 ml)
  3. washThe combined organic phases were washed with sat. NaCl solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-410a35576ba7456785f4e43500c651e0
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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