Hexamethyldisilazane → HCID 18626641, 화합물

HRID 1860150노트

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HRID 1860150 반응식
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[NH:32][Si](C)(C)C>CN(C)C=O.C(Cl)Cl.CO>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=2)[C:8]([NH2:32])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 3

HCID 13838HexamethyldisilazaneHCID 65578Oxalyl chlorideHCID 120105413-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid

생성물 1

HCID 18626641HCID 18626641, 화합물수율 47%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 887Methanol용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A mixture of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid (300 mg, 0.88 mmol) and 1 drop of N,N-dimethylformamide in methylene chloride (2 mL) was cooled to 0° C. and then slowly treated with oxalyl chloride (84 μL, 0.97 mmol). The reaction mixture was stirred at 0° C. for 10 min and then stirred at 25° C. for 1 h. The resulting reaction mixture was then treated dropwise with 1,1,1,3,3,3-hexamethyldisilazane (560 μL, 2.64 mmol) and subsequently stirred at 25° C. for 15 h. The resulting reaction mixture was diluted with methylene chloride (20 mL) and methanol (15 mL) and then washed with a 5% aqueous sulfuric acid solution (20 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/3 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionamide (140 mg, 47%) as a yellow foam: mp 72-76° C. (foam to gel); FAB-HRMS m/e calcd for C15H20N2O5S (M+H)+341.1172, found 341.1181.

후처리

  1. stirringstirred at 25° C. for 1 h
  2. customThe resulting reaction mixture
  3. stirringsubsequently stirred at 25° C. for 15 h
  4. customThe resulting reaction mixture
  5. washwashed with a 5% aqueous sulfuric acid solution (20 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5fb7e2748bba42e4a26e3937968ed245
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528543B1

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