Cesium carbonate → 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine methyl ester

HRID 276111

반응식

HRID 276111 반응식
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:12])[CH:7](Br)[CH2:8][CH2:9][CH3:10].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][SH:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCC.C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:12])[CH:7]([S:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[CH2:8][CH2:9][CH3:10]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 21226206Ethyl acetate hexane2회HCID 229508312-bromopentanoyl-(L)-homophenylalanine methyl ester

생성물 1

HCID 229508282-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine methyl ester

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

Combine 2-bromopentanoyl-(L)-homophenylalanine methyl ester (3.6 g, 10 mmol), 4-methyoxybenzylmercaptan (3.48 mL, 25 mmol), and tetrabutylammonium iodide (about 50 mg) in dimethylformamide (10 mL). Degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add cesium carbonate (4.10 g, 12.5 mmol). After 15 hours, partition the reaction mixture between water and methyl t-butyl ether, saturate the aqueous layer with sodium chloride. Extract the aqueous layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 4/1 hexane/ethyl acetate and then 2.5/1 hexane/ethyl acetate to give the title compound: Rf=0.44 (silica gel, 2.5/1 hexane/ethyl acetate).

후처리

  1. customDegas
  2. custompartition the reaction mixture between water and methyl t-butyl ether
  3. concentrationsaturate the aqueous layer with sodium chloride
  4. extractionExtract the aqueous layer with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

출처 및 근거

ORD 기록
ord-d1385ca9dc824c218ae0cd8094c64e04
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352976B1

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