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Imidazole → (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

HRID 13431
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HRID 13431 반응식
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.CN(C)C=O.[CH2:29]([O:36][C:37]([N:39]1[CH2:43][C@H:42]([OH:44])[CH2:41][C@@H:40]1[C:45]([OH:47])=[O:46])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)(=O)C>[CH2:29]([O:36][C:37]([N:39]1[CH2:43][C@H:42]([O:44][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:41][C@@H:40]1[C:45]([OH:47])=[O:46])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 688416(2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

생성물 1

HCID 67482921(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

2.32 g of tert-butyldiphenylsilyl chloride and 2.32 g of imidazole were added in order to a dimethylformamide (60 ml) solution of 3.61 g of (2R,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, washed with aqueous saturated ammonium chloride and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2) to obtain the entitled compound.

후처리

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with aqueous saturated ammonium chloride and saturated saline in order
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2)
  7. customto obtain the entitled compound

출처 및 근거

ORD 기록
ord-72690fe8b46b401484ce85a4f574b9e7
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728025B2

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