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(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → tert-butyl (2S,3R)-4-(3-(diethylamino)benzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

HRID 2071176
ノート
印刷プレビュー

反応式

HRID 2071176 の反応式
[Al](OS(C(F)(F)F)(=O)=O)(OS(C(F)(F)F)(=O)=O)OS(C(F)(F)F)(=O)=O.[NH2:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=1)[N:31]([CH2:34][CH3:35])[CH2:32][CH3:33].[O:39]1[CH2:41][C@@H:40]1[C@@H:42]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CCOC(C)=O.O>[CH2:34]([N:31]([CH2:32][CH3:33])[C:30]1[CH:29]=[C:28]([CH:38]=[CH:37][CH:36]=1)[CH2:27][NH:26][CH2:41][C@@H:40]([OH:39])[C@@H:42]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:55])([CH3:54])[CH3:56])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH3:35]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneHCID 16684924Al(III) triflateHCID 392370373-(aminomethyl)-N,N-diethylaniline

生成物 1

HCID 59569656tert-butyl (2S,3R)-4-(3-(diethylamino)benzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate収率 22%

試薬・触媒・溶媒 2

HCID 962Water
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

Al(OTf)3 (0.0168 g, 0.036 mmol, 5 mol %) was added to a flask charged with 3-(aminomethyl)-N,N-diethylaniline (0.19 g, 1.07 mmol, 1.5 eq) under Ar. After stirring for 10 min tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (0.187 g, 0.71 mmol, 1 eq) was added and the mixture was heated to 70° C. for 1 h. After cooling to room temperature the residue was dissolved in EtOAc with a few drops of water. After 20 min of vigorous stirring the mixture was filtered through cotton and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.0682 g (0.154 mmol, 22% yield) of the product.

後処理

  1. additionwas added
  2. temperatureAfter cooling to room temperature the residue
  3. filtrationwas filtered through cotton
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent was removed in vacuo
  7. customPurification via flash chromatography

出典と根拠

ORDレコード
ord-06b7f7cab80a4d7989d8d051ed5376fc
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299267B2

反応ノート

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