Sodium Bicarbonate → 1-[[(6RS)-6-(N-tert-Butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

HRID 352839노트

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HRID 352839 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:20]O)[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.FC(F)(F)C(O)=O.[Cl:40][C:41]1[CH:42]=[C:43]2[C:48](=[CH:49][CH:50]=1)[CH:47]=[C:46]([S:51]([N:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1)(=[O:53])=[O:52])[CH:45]=[CH:44]2.C(=O)(O)[O-].[Na+]>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH2:20][N:57]3[CH2:56][CH2:55][N:54]([S:51]([C:46]4[CH:45]=[CH:44][C:43]5[C:48](=[CH:49][CH:50]=[C:41]([Cl:40])[CH:42]=5)[CH:47]=4)(=[O:53])=[O:52])[CH2:59][CH2:58]3)[CH:14]=[CH:13][C:12]=2[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 22709613Tert-butyl ((6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-YL)methyl)carbamateHCID 22710058HCID 22710058, 화합물HCID 178418287HCID 178418287, 화합물

생성물 1

HCID 227099231-[[(6RS)-6-(N-tert-Butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8471Triethylamine용매

실험 절차

In dichloromethane (5 ml), the (2RS)-2-(N-tert -butoxycarbonylaminomethyl)-6-hydroxymethyl-1,2,3,4-tetrahydronaphthalene (0.19 g) was dissolved. Pyridinium chlorochromate (0.17 g) was added to the resulting solution, followed by stirring at room temperature for 2 hours. The reaction mixture was purified as it was by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby a colorless solid (0.16 g) was obtained. The resulting solid was dissolved in dichloromethane (8 ml), followed by the addition of 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine trifluoroacetate (0.24 g), triethylamine (80.0 μl) and sodium triacetoxyboron hydride (0.17 g). The resulting mixture was stirred at room temperature for 16 hours under an argon gas atmosphere. An aqueous solution of sodium bicarbonate was added to the reaction mixture. The resulting mixture was diluted with dichloromethane to separate the organic layer. The organic layer was dried over sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1), whereby a colorless viscous liquid (0.33 g, 86%) was obtained.

후처리

  1. customThe reaction mixture was purified as it
  2. customwas obtained
  3. stirringThe resulting mixture was stirred at room temperature for 16 hours under an argon gas atmosphere
  4. customto separate the organic layer
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1), whereby a colorless viscous liquid (0.33 g, 86%)
  9. customwas obtained

출처 및 근거

ORD 기록
ord-152a82ff36c54c968a59156ff6695911
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747023B1

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