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Cesium carbonate → 5(S)-[1(S)-(Boc-Amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]dihydrofuran-2-(3H)-one

HRID 1377198
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HRID 1377198 반응식
[C:1]([NH:8][C@H:9]([C@H:18]1[O:22][C:21](=[O:23])[CH2:20][CH2:19]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:30][O:31][CH2:32][CH2:33]I>CN(C=O)C.O1CCOCC1>[C:1]([NH:8][C@H:9]([C@H:18]1[O:22][C:21](=[O:23])[CH2:20][CH2:19]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:33][CH2:32][O:31][CH3:30])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 791361-Iodo-2-methoxyethane2회HCID 539985235(S)-[1(S)-(Boc-amino)-2-(p-hydroxyphenyl)ethyl]dihydrofuran-2-(3H)-one2회

생성물 1

HCID 541918735(S)-[1(S)-(Boc-Amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]dihydrofuran-2-(3H)-one

시약·촉매·용매 1

HCID 217120691,4-dioxane N,N-dimethylformamide
용매

실험 절차

3.17 g (9.86 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-hydroxyphenyl)ethyl]dihydrofuran-2-(3H)-one in 190 ml of DMF/dioxane, 1:1, are treated, under an N2 atmosphere, with 6.4 g (19.7 mmol) of Cs2CO3 and 2.0 g (9.86 mmol) of 2-methoxyethyl iodide. Since HPLC indicates that unreacted 5(S)-[1(S)-(Boc-amino)-2-(p-hydroxyphenyl)ethyl]dihydrofuran-2-(3H)-one is still present after 18 h at RT, a further 1.2 g of 2-methoxyethyl iodide are added in portions. As soon as HPLC indicates that the reaction is complete, the reaction mixture is poured onto 190 ml of ice-water, and the whole is extracted 3× with methylene chloride. The organic phases are washed with water and saline, dried with Na2SO4 and evaporated. Stirring up the residue with hexane in an ultrasonication bath affords the title compound: TLC Rf (D)=0.08; FAB-MS (M+H)+ =380.

후처리

  1. extractionthe whole is extracted 3× with methylene chloride
  2. washThe organic phases are washed with water and saline
  3. dry with materialdried with Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-dc40c1d2846441af9b1c9ea36520becd
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05663200

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