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Pyridine → (S,E)-allyl 2-(2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate

HRID 513359
ノート
印刷プレビュー

反応式

HRID 513359 の反応式
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].[NH2:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[C:12]([O:26][CH3:27])=[CH:11][C:10]=1[C:28]([N:30]1[CH:34]=[C:33](/[CH:35]=[CH:36]/[CH3:37])[CH2:32][C@H:31]1[CH2:38][O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])=[O:29].N1C=CC=CC=1>C(Cl)Cl>[Si:40]([O:39][CH2:38][C@@H:31]1[CH2:32][C:33](/[CH:35]=[CH:36]/[CH3:37])=[CH:34][N:30]1[C:28]([C:10]1[CH:11]=[C:12]([O:26][CH3:27])[C:13]([O:15][Si:16]([CH:17]([CH3:19])[CH3:18])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:21])[CH3:22])=[CH:14][C:9]=1[NH:8][C:2](=[O:3])[O:4][CH2:5][CH:6]=[CH2:7])=[O:29])([C:43]([CH3:44])([CH3:46])[CH3:45])([CH3:41])[CH3:42]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 86717762(S,E)-(2-amino-5-methoxy-4-(triisopropylsilyloxy)phenyl)(2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrol-1-yl)methanone

生成物 1

HCID 86717763(S,E)-allyl 2-(2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate収率 100%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

Allyl chloroformate (0.83 g, 6.88 mmol, 1.1 eq) was added to a solution of the amine 7 (3.6 g, 6.26 mmol, 1.0 eq) in dry DCM (80 mL) containing dry pyridine (1.09 g, 13.77 mmol, 2.2 eq) at −78° C. The dry ice was removed and the reaction mixture allowed to warm to room temperature. After stirring for a further 15 minutes, LC/MS indicated complete reaction. The organic phase was washed successively with 0.01N HCl (50 mL), saturated sodium bicarbonate (50 mL), brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure to leave a pale yellow oil which was used in the next step without further purification (4.12 g, assumed 100% yield). LC/MS (4.862 min (ES+)), m/z: 659.2 [M+H]+.

後処理

  1. customThe dry ice was removed
  2. customreaction
  3. washThe organic phase was washed successively with 0.01N HCl (50 mL), saturated sodium bicarbonate (50 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto leave a pale yellow oil which
  8. customwas used in the next step without further purification (4.12 g, assumed 100% yield)
  9. customLC/MS (4.862 min (ES+)), m/z

出典と根拠

ORDレコード
ord-4b3e9c32ebca4a0c96cb8f86d67c190f
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102704B2

反応ノート

読み込み中…

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