Sodium Iodide → iodomethyl 5(N-CBz-L-valyloxy)-2,2-dimethylvalerate

HRID 1170601노트

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HRID 1170601 반응식
[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:29])([CH3:28])[C:23]([O:25][CH2:26]Cl)=[O:24])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[I-:30].[Na+]>C(#N)C>[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:29])([CH3:28])[C:23]([O:25][CH2:26][I:30])=[O:24])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

참가 물질

4

반응물 2

HCID 5238Sodium IodideHCID 23387570chloromethyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate

생성물 1

HCID 23387406iodomethyl 5(N-CBz-L-valyloxy)-2,2-dimethylvalerate수율 91.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

To a solution of chloromethyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate (3.85 g, 9 mmol) in acetonitrile (50 mL), was added sodium iodide (5.40 g, 36 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2 and washed with aqueous sodium thiosulfate (0.1 M). The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was column chromatographed (silica gel, 1% MeOH in CH2Cl2), to give 4.26 g of iodomethyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate

후처리

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with aqueous sodium thiosulfate (0.1 M)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed (silica gel, 1% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-a9d21487316b404ca01f91cd745f1d09
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825238B2

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