Benzylamine → HCID 58504674, 화합물

HRID 2367315노트

반응식

HRID 2367315 반응식
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH:12]([CH3:13])[CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:13][CH:12]1[CH2:11][CH:10]([C:14]([NH:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:16])[CH2:9][N:8]1[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]

참가 물질

6

반응물 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 585047701,3-Pyrrolidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester

생성물 1

HCID 58504674HCID 58504674, 화합물수율 135.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-3-pyrrolidinecarboxylic acid (0.9 g, 3.93 mmol) in CH2Cl2 (15 mL) at room temperature was added Hunig's base (0.89 mL, 5.10 mmol, 1.3 equiv) and benzylamine (0.56 mL, 5.10 mmol, 1.3 equiv) in one portion. The resulting mixture was chilled in an ice bath, followed by addition of HATU (1.64 g, 4.32 mmol, 1.1 equiv) in one portion, and the reaction mixture was stirred in the ice bath for 30 minutes. The mixture was filtered through celite, and rinsed with CH2Cl2. The filtrate was washed with water and dried over Na2SO4, followed by filtration and concentration in vacuo. The resulting residue was purified by silica gel column chromatography resulting in 1.70 g of the title compound as an oil. The ratio of cis/trans isomers could not be determined. LC-MS (ES) m/z=319 [M+H]+.

후처리

  1. temperatureThe resulting mixture was chilled in an ice bath
  2. filtrationThe mixture was filtered through celite
  3. washrinsed with CH2Cl2
  4. washThe filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfollowed by filtration and concentration in vacuo
  7. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3757bc4ce67a47aeab5fe6e97d70ac83
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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