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Triacetoxyperiodinane → Cbz-D-Phenylalaninal

HRID 340442
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인쇄 미리보기

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HRID 340442 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

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

생성물 1

HCID 10779332Cbz-D-Phenylalaninal수율 88.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b8a012688812459fba1eeb23131bb807
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895585B2

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