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Methyl iodide → 4-cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide

HRID 77412
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HRID 77412 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:26]=[CH:25][C:9]([C:10]([NH:12][C@H:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=[O:24])[CH:19]=4)[CH2:14]3)=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[CH3:27]I.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:26]=[CH:25][C:9]([C:10]([N:12]([C@H:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=[O:24])[CH:19]=4)[CH2:14]3)[CH3:27])=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1
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참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 867627484-Cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide

생성물 1

HCID 867627474-cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A mixture of 4-cyclopropylmethoxy-N—((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-benzamide (2.70 g), methyl iodide (0.534 ml) and DMF (100 ml) was admixed at 0° C. with sodium hydride (55% in paraffin oil; 0.34 g) in portions. After 15 minutes, the reaction mixture was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel (eluent: 30% n-heptane in ethyl acetate). The product was thus obtained with the molecular weight of 363.46 (C23H25NO3); MS (ESI): 364 (M+H+).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (eluent: 30% n-heptane in ethyl acetate)
  5. customThe product was thus obtained with the molecular weight of 363.46 (C23H25NO3)

출처 및 근거

ORD 기록
ord-d659b20a3ad64c6dbbd147f48f3c3ecc
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841290B2

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