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Triacetoxyperiodinane → Cbz-D-Phenylalaninal

HRID 2406697
ノート
印刷プレビュー

反応式

HRID 2406697 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31](=[O:43])[NH:32][C@H:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:34][OH:35])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:23]([O:30][C:31](=[O:43])[NH:32][C@H:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:34]=[O:35])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 736170Benzyl hydrogen (1-hydroxy-3-phenylpropan-2-yl)carbonimidate

生成物 1

HCID 10779332Cbz-D-Phenylalaninal収率 88.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dess-Martin periodinane (849 mg) was added to a dichloromethane (20 ml) solution containing benzyl((2R)-1-hydroxy-3-phenylpropan-2-yl)carbamate (571 mg), followed by stirring at room temperature for 3 hours and 30 minutes. Insoluble matter was removed by filtration, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 2:1), and a white solid of benzyl((2R)-1-oxo-3-phenylpropan-2-yl)carbamate (501 mg) was thus obtained.

後処理

  1. customInsoluble matter was removed by filtration
  2. distillationthe solvent was distilled away under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 2:1)

出典と根拠

ORDレコード
ord-86d6abba17f240198dada839ca8c4e84
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08809371B2

反応ノート

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