Sulfuric Acid → (3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one

HRID 2207646노트

반응식

HRID 2207646 반응식
[CH3:1][N:2]1[CH2:6][CH2:5][C@@:4]([NH:27]C(=O)OC(C)(C)C)([CH2:7][C:8]#[C:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=3)[CH:13]=[CH:12][N:11]=2)[C:3]1=[O:35].OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C>[NH2:27][C@@:4]1([CH2:7][C:8]#[C:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH2:5][CH2:6][N:2]([CH3:1])[C:3]1=[O:35]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 89649351tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-3-yl]carbamate

생성물 1

HCID 89648960(3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one수율 97.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

A solution of tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-3-yl]carbamate (8.91 g, 18.19 mmol) (which may be prepared as described in Description 106) in 1,4-dioxane (70 mL) was cooled in an ice bath and treated dropwise with conc. H2SO4 (7.4 mL, 93.22 mmol). The mixture was allowed to reach room temperature and after 45 mins, the mixture was again cooled in an ice bath and treated cautiously with satd. aq. Na2CO3 solution (˜150 ml). The mixture was diluted with ethyl acetate (200 ml) and the product was extracted into ethyl acetate (2×150 ml). The combined organic extracts were dried (Na2SO4) and concentrated to give the title compound (D107) as an orange oil (6.88 g, 97%) consistent spectroscopically with that prepared by Method A.

후처리

  1. temperaturethe mixture was again cooled in an ice bath
  2. additiontreated cautiously with satd
  3. extractionthe product was extracted into ethyl acetate (2×150 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5a9f1083b1194bd5b250105321263baa
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376436B2

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