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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
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HRID 513359 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 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)phenylcarbamate수율 100%

시약·촉매·용매

1
HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-4b3e9c32ebca4a0c96cb8f86d67c190f
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102704B2

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