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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
ノート
印刷プレビュー

反応式

HRID 403597 の反応式
[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]
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 8471TriethylamineHCID 94429TriphosgeneHCID 584852601-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b9c2bb416f3e478b98f69f49e89154e5
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748444B2

反応ノート

読み込み中…

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