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Hydrochloric Acid → (3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine

HRID 1253417
ノート
印刷プレビュー

反応式

HRID 1253417 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH2:16][OH:17])[C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH2:16][O:17][S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 23635905(3S,4S)-Benzyl 3-((tert-butoxycarbonyl)amino)-4-(hydroxymethyl)pyrrolidine-1-carboxylate

生成物 1

HCID 86618513(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 1049Pyridine溶媒

実験手順

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-hydroxymethylpyrrolidine (5.00 g, 14.3 mmol) was dissolved in pyridine (50 mL). p-Toluenesulfonyl chloride (4.08 g, 21.4 mmol) and 4-(N,N-dimethyl)aminopyridine (174 mg, 1.43 mmol) were added thereto at room temperature, and the resultant mixture was stirred under a nitrogen atmosphere for 24 hours. Under cooling, ethyl acetate (200 mL) and 1 mol/L hydrochloric acid (200 mL) were added thereto, followed by extraction with ethyl acetate (200 mL×2). The organic layer was washed sequentially by 1 mol/L hydrochloric acid (100 mL), saturated sodium hydrogencarbonate (100 mL), and saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:1), to thereby yield the title compound as a colorless amorphous substance (6.27 g, 87%).

後処理

  1. temperatureUnder cooling
  2. extractionfollowed by extraction with ethyl acetate (200 mL×2)
  3. washThe organic layer was washed sequentially by 1 mol/L hydrochloric acid (100 mL), saturated sodium hydrogencarbonate (100 mL), and saturated brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:1)

出典と根拠

ORDレコード
ord-36589a66f69344c191252f9e070996e1
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08455482B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート