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Sodium Carbonate → (IR)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide

HRID 478160
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인쇄 미리보기

반응식

HRID 478160 반응식
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:17][C:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.[OH-].[Na+]>C(Cl)Cl.O>[OH:9][CH2:8][C@H:7]([NH:10][C:21]([C:18]1([Br:17])[CH2:20][CH2:19]1)=[O:22])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 109102061-Bromocyclopropane-carboxylic acid chloride

생성물 1

HCID 21350875(IR)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide수율 71.2%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매

실험 절차

739 mg of D-(−)-α-phenylglycinol is dissolved in 27 ml of methylene chloride, and 678 mg of sodium carbonate is added to 11 ml of water and 1.09 g of acid chloride 107 at room temperature. It is stirred overnight and then mixed with methanolic sodium hydroxide solution, the organic phase is separated, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 1.09 g of (1R)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide 110 is isolated as a colorless oil.

후처리

  1. customthe organic phase is separated
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-e6928768b20a42ef83d70c01fd8ee553
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06642218B2

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