Phenyltrimethylsilane → trans-1-Benzoyl-4-phenyl-l-proline

HRID 1165977

반응식

HRID 1165977 반응식
[C:1]([N:9]1[CH2:16][C@@H:15](OS(C)(=O)=O)[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([Si](C)(C)C)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClC1C=CC=CC=1Cl>[C:1]([N:9]1[CH2:16][C@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 69849PhenyltrimethylsilaneHCID 6451240Aluminum(III) ChlorideHCID 11120569cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline

생성물 1

HCID 46864073trans-1-Benzoyl-4-phenyl-l-proline

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

실험 절차

A suspension of powdered (cis)-1-benzoyl-4-mesyloxy-L-proline (250 mg, 0.8 mmole) in 1,2-dichlorobenzene (3 ml) was stirred under argon and treated with phenyltrimethylsilane (1 ml, 5.8 mmole) followed by aluminum trichloride (383 mg, 2.87 mmole). The reaction was stirred overnight and an aliquot was removed, quenched into 1N HCl and extracted with ethyl acetate. Analysis of the organic layer by tlc showed the presence of:

후처리

  1. stirringThe reaction was stirred overnight
  2. customan aliquot was removed
  3. customquenched into 1N HCl
  4. extractionextracted with ethyl acetate

출처 및 근거

ORD 기록
ord-8c8b1083c13a4d1e80804b6e0001a43a
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04912231

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