Diisopropylethylamine → rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide

HRID 220318노트

반응식

HRID 220318 반응식
[CH3:1][O:2][CH2:3][C:4]([CH2:9][O:10][CH3:11])([CH3:8])[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:45][N:46]([CH2:64][CH2:65][CH2:66][NH:67][CH3:68])[CH2:47][CH2:48][C:49]1([OH:63])[CH2:54][CH:53]2[CH2:55][CH2:56][CH:50]1[CH:51]=[C:52]2[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C(Cl)Cl>[OH:63][C@@:49]1([CH2:48][CH2:47][N:46]([CH3:45])[CH2:64][CH2:65][CH2:66][N:67]([CH3:68])[C:5](=[O:7])[C:4]([CH2:3][O:2][CH3:1])([CH3:8])[CH2:9][O:10][CH3:11])[CH2:54][C@H:53]2[CH2:55][CH2:56][C@@H:50]1[CH:51]=[C:52]2[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

참가 물질

6

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 219119313-Methoxy-2-(methoxymethyl)-2-methylpropanoic acidHCID 68413377rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

생성물 1

HCID 68413389rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide수율 90.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 65 mg 3-methoxy-2-methoxymethyl-2-methyl-propionic acid in 0.5 mL DCM was added 0.14 mL DIPEA followed by 133 mg HATU. The resulting mixture was stirred at rt for 20 min before 88 mg of rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol, dissolved in 1 mL DCM was added. After stirring overnight the reaction was quenched with water. The water phase was extracted with DCM, the combined organic phases were washed with brine, dried and concentrated in vacuo. The residue was purified by CC with EtOAc-MeOH (3:1) to obtain 115 mg of rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide as colorless oil.

후처리

  1. additionwas added
  2. customwas quenched with water
  3. extractionThe water phase was extracted with DCM
  4. washthe combined organic phases were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by CC with EtOAc-MeOH (3:1)

출처 및 근거

ORD 기록
ord-93485bb4680b41159d26694fe08bc57a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202885B2

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