(S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid → HCID 58557467、化合物

HRID 1969589ノート

反応式

HRID 1969589 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:17]([C:19]1[N:20]=[C:21]2[CH:27]=[CH:26][N:25]([S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]2=[N:23][CH:24]=1)[NH2:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[O:16]=[C:14]([NH:18][NH:17][C:19]1[N:20]=[C:21]2[CH:27]=[CH:26][N:25]([S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]2=[N:23][CH:24]=1)[CH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1

参加物

6

反応物 3

HCID 1502098(S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

生成物 1

HCID 58557467HCID 58557467、化合物収率 111.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)-3-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.756 g, 3.30 mmol, AstaTech) and 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (1.0 g, 3.3 mmol, Example #1, Step D) in DMF (33 mL) was added TEA (1.38 mL, 9.89 mmol) followed by the addition of HATU (1.25 g, 3.30 mmol). The resulting mixture was stirred at ambient temperature for about 15 h then concd under reduced pressure. The residue was taken up in EtOAc (100 mL) and washed with water (100 mL). The organic portion was separated, washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concd under reduced pressure to give (S)-tert-butyl 3-(2-oxo-2-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinyl)ethyl)pyrrolidine-1-carboxylate as a sticky brown solid (1.90 g, 100%). This material was used without further purification: LC/MS (Table 1, Method c) Rt=1.38 min; MS m/z: 515 (M+H)+.

後処理

  1. washwashed with water (100 mL)
  2. customThe organic portion was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-67523f668e80434897f830a20aa5fe94
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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