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Triacetoxyperiodinane → Cbz-D-Phenylalaninal

HRID 340442
ノート
印刷プレビュー

反応式

HRID 340442 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-b8a012688812459fba1eeb23131bb807
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895585B2

反応ノート

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