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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
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반응식

HRID 2071176 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water
촉매
HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-06b7f7cab80a4d7989d8d051ed5376fc
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299267B2

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