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

HRID 2207646ノート

反応式

HRID 2207646 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a9f1083b1194bd5b250105321263baa
出典データセット
uspto-grants-2016_06
特許番号
US09376436B2

反応ノート

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