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Hydrochloric Acid → 2-(1-Methylsulfanyl-2-phenethylcarbamoyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1582732
ノート
印刷プレビュー

反応式

HRID 1582732 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([S:19][CH3:20])[CH:14]([C:16]([OH:18])=O)[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.C1C=C2N=NN(O)C2=CC=1.O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([S:19][CH3:20])[CH:14]([C:16](=[O:18])[NH:29][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 693253742-(2-Carboxy-1-methylsulfanyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 695513572-(1-Methylsulfanyl-2-phenethylcarbamoyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
収率 43%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of the crude 2-(2-carboxy-1-methylsulfanyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (223 mg) obtained above in CH2Cl2 (3 ml) was added phenethylamine(0.18 ml, 1.41 mmol), WSCI monohydrochloride(203 mg, 1.06 mmol), HOBt monohydrate(162 mg, 1.06 mmol) and diisopropylethylamine(0.37 ml, 2.12 mmol) at room temperature. After being stirred at room temperature for 4.5 hr, the mixture was quenched with 1N HCl (20 ml), extracted with AcOEt, dried (MgSO4) and concentrated in vacuo to give a crude oil, which was purified by flash column chromatography (hexane:AcOEt=3:1) to give 2-(1-methylsulfanyl-2-phenethylcarbamoyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as an oil(123 mg, 43%).

後処理

  1. customthe mixture was quenched with 1N HCl (20 ml)
  2. extractionextracted with AcOEt
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a crude oil, which
  6. customwas purified by flash column chromatography (hexane:AcOEt=3:1)

出典と根拠

ORDレコード
ord-20f8d75f2edb4f4d8d44c349e813191a
出典データセット
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06737409B2

反応ノート

読み込み中…

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