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Tetrahydrofuran → (2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid

HRID 1025329
ノート
印刷プレビュー

反応式

HRID 1025329 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@H:16]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])(=[O:20])=[O:19])[CH2:15][C@H:14]3[C:28]([O:30]C)=[O:29])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1COCC1.O.[OH-].[Li+]>O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@H:16]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])(=[O:20])=[O:19])[CH2:15][C@H:14]3[C:28]([OH:30])=[O:29])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86762435(2S,4R)-methyl 1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylate

生成物 1

HCID 68503876(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 962Water溶媒

実験手順

Under an atmosphere of argon, (2S,4R)-methyl 1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylate (1.5 g, 3.11 mmol, Eq: 1.00) was combined with THF (20 ml) to give a light yellow solution. Then lithium hydroxide monohydrate (196 mg, 4.66 mmol, Eq: 1.5) in 4 ml water and 4 ml methanol was added. The reaction was stirred for 2 h at RT. The solvents were evaporated. The reaction was extracted with ethyl acetate, H2O and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a white foam (1.52 g, 97.1%, MS (m/e)=468.2 [M+H+]; MS (m/e)=466.1 [M−H+]).

後処理

  1. customto give a light yellow solution
  2. customThe solvents were evaporated
  3. extractionThe reaction was extracted with ethyl acetate, H2O and brine
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-06a34d72c3b74135a2d27514e9bdaab4
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729061B2

反応ノート

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