Diisopropylethylamine → 4-((t-Butoxycarbonyl)(methyl)amino)-4'-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl

HRID 1519667노트

반응식

HRID 1519667 반응식
Cl.[CH3:2][NH:3][C:4](=[O:12])[C@H:5]([C:8](=[O:11])[O:9][CH3:10])[NH:6][CH3:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:46]([O:50][C:51]([N:53]([CH3:69])[C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][C:63]([C:66](O)=[O:67])=[CH:62][CH:61]=2)=[CH:56][CH:55]=1)=[O:52])([CH3:49])([CH3:48])[CH3:47]>O.C(OCC)(=O)C.CN(C=O)C>[C:46]([O:50][C:51]([N:53]([CH3:69])[C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][C:63]([C:66]([N:6]([CH:5]([C:4]([NH:3][CH3:2])=[O:12])[C:8]([O:9][CH3:10])=[O:11])[CH3:7])=[O:67])=[CH:62][CH:61]=2)=[CH:56][CH:55]=1)=[O:52])([CH3:47])([CH3:48])[CH3:49]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712682544'-((t-Butoxycarbonyl)(methyl)amino)biphenyl-4-carboxylic acidHCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride2회

생성물 1

HCID 712682134-((t-Butoxycarbonyl)(methyl)amino)-4'-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl수율 51%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 90 mg), HATU (0.17 g) and DIPEA (0.16 mL) were added to a DMF (2.0 mL) solution of 4′-((t-butoxycarbonyl)(methyl)amino)biphenyl-4-carboxylic acid (0.10 g), as obtained in Example 2-(2), and the mixture was stirred for 16 hours at room temperature. Ethyl acetate and water were added to the reaction mixture to isolate the organic layer, and the extract was washed sequentially with water and brine. The system was dried over anhydrous sodium sulfate and, after separation of the desiccant by filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to obtain 4-((t-butoxycarbonyl)(methyl)amino)-4′-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl (white foam) (73 mg, 51%).

후처리

  1. customto isolate the organic layer
  2. washthe extract was washed sequentially with water and brine
  3. dry with materialThe system was dried over anhydrous sodium sulfate
  4. customafter separation of the
  5. filtrationdesiccant by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3)

출처 및 근거

ORD 기록
ord-4a328d5ec0564b43ab762dfde2cd9f1b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073821B2

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