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Diisopropylethylamine → tert-butyl (1S)-1-{[[(1S,2E)-3-cyano-1-isopropyl-2-propenyl](methyl)amino]carbonyl}-2,2-dimethylpropylcarbamate

HRID 133823
ノート
印刷プレビュー

反応式

HRID 133823 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:24]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2N=N1.C[CH2:51][N:52](C(C)C)C(C)C.[CH3:59]CCCCC.CCOCC>ClCCl.FC(F)(F)C(O)=O.CC(C)[C@H](NC)/C=C/C#N>[C:28](/[CH:29]=[CH:30]/[C@@H:31]([N:52]([CH3:51])[C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH:32]([CH3:27])[CH3:59])#[N:24]
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 81531DiisopropylethylamineHCID 2724699PyBOPHCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 21584099Diethylether hexane

生成物 1

HCID 86596607tert-butyl (1S)-1-{[[(1S,2E)-3-cyano-1-isopropyl-2-propenyl](methyl)amino]carbonyl}-2,2-dimethylpropylcarbamate

試薬・触媒・溶媒 2

HCID 86596608
(E,4S)-5-methyl-4-(methylamino)-2-hexenenitrile trifluoroacetic acid
触媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of (E,4S)-5-methyl-4-(methylamino)-2-hexenenitrile trifluoroacetic acid (−1.68 mmol, from Reference Example 14), 2-tert-Butoxycarbonylamino-3,3-dimethyl-butyric acid (389 mg, 1.68 mmol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP, 916 mg, 1.76 mmol) in dichloromethane (5 mL) at OC is added Hunig's base (0.877 mL, 5.04 mmol). After 5 min the cooling bath is removed. After 24 h 5% aqueous citric acid is added. The aqueous phase is washed with dichloromethane three times. The combined organic extracts are dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oil. Chromatography (silica gel, hexane/ether) gave the title compound as a yellow foam (200 mg). MS (ES): m/z 352.0 (M+H)

後処理

  1. customAfter 5 min the cooling bath is removed
  2. additionAfter 24 h 5% aqueous citric acid is added
  3. washThe aqueous phase is washed with dichloromethane three times
  4. dry with materialThe combined organic extracts are dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give an oil

出典と根拠

ORDレコード
ord-442d842f365446f59ffd4f700dcc6777
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07390910B2

反応ノート

読み込み中…

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