Potassium Hydroxide → (R)-3-(2-Methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1253653ノート

反応式

HRID 1253653 の反応式
[OH-].[K+].[CH3:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[C:6]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20]C)=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7]>C(O)C.O>[CH3:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[C:6]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 59505253(R)-Methyl 3-(2-methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

生成物 1

HCID 59505670(R)-3-(2-Methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid収率 88%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

KOH (1 mol/laq) (2 eq.) was added to a suspension of (R)-methyl 3-(2-methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-09) (0.61 mmol, 1 eq.) in a mixture of ethanol (3.6 ml) and water (0.8 ml). The reaction mixture was stirred at room temperature overnight. Ethanol was removed in vacuo and the aqueous residue was diluted with diethyl ether and dist. water. The phases were separated and the aqueous phase was acidified with 1N HCl to pH 3 and then extracted 4× with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated in vacuo to yield the desired product (E-09). Yield: 88%

後処理

  1. customEthanol was removed in vacuo
  2. additionthe aqueous residue was diluted with diethyl ether and dist
  3. customThe phases were separated
  4. extractionextracted 4× with ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1c2f1c271dcc4bc695537e67ac02132f
出典データセット
uspto-grants-2013_06
特許番号
US08455475B2

反応ノート

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