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

HRID 989949ノート

反応式

HRID 989949 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-955ae12262e64ef8935df0c5020032b3
出典データセット
uspto-grants-2002_10
特許番号
US06458772B1

反応ノート

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