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

HRID 1025329
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HRID 1025329 반응식
[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
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참가 물질

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

생성물 1

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

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

실험 절차

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+]).

후처리

  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

출처 및 근거

ORD 기록
ord-06a34d72c3b74135a2d27514e9bdaab4
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729061B2

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