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Triethylamine → 6-allyl-3-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one

HRID 403597
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인쇄 미리보기

반응식

HRID 403597 반응식
[Si:1]([O:8][C:9]([CH3:27])([CH3:26])[C@@H:10]([NH:12][CH2:13][CH2:14][C:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([OH:19])[CH2:16][CH:17]=[CH2:18])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:16]([C:15]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:19][C:36](=[O:38])[N:12]([C@H:10]([C:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])([CH3:26])[CH3:27])[CH3:11])[CH2:13][CH2:14]1)[CH:17]=[CH2:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 584852601-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol

생성물 1

HCID 584852646-allyl-3-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one수율 52.1%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

To a solution of 1-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol (550 mg, 1.41 mmol) and Et3N (1.4 g, 14.1 mmol) in CH2Cl2 (5 mL) was added triphosgene (138 mg, 0.46 mmol) at 0° C. The formed mixture was heated to reflux overnight. The mixture was washed with water. The organic phase was separated and concentrated to give the crude product which was purified by TLC to afford 6-allyl-3-((2S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one (100 mg, 17%). 1H NMR (CDCl3): 0.00 (s, 6H), 0.73 (s, 9H), 1.08 (s, 3H), 1.12 (d, 3H), 1.21 (s, 3H), 2.83 (q, 1H), 4.08 (brs, 1H).

후처리

  1. temperatureThe formed mixture was heated
  2. temperatureto reflux overnight
  3. washThe mixture was washed with water
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by TLC

출처 및 근거

ORD 기록
ord-b9c2bb416f3e478b98f69f49e89154e5
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748444B2

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