Diisopropylethylamine → (2S,4R)-tert-butyl 4-(benzyloxycarbonylamino)-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 1630080ノート

反応式

HRID 1630080 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([OH:26])=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[N:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:51][C:52]1[CH:65]=[CH:64][C:55]([O:56]NC2C=CC=CC=2)=[CH:54][CH:53]=1.[CH3:66]CN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24](=[O:26])[NH:41][C:36]2[CH:37]=[CH:38][C:39]([O:56][C:55]3[CH:64]=[CH:65][C:52]([F:51])=[CH:53][CH:54]=3)=[CH:40][CH:66]=2)[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 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 11660571(2S,4R)-4-(((benzyloxy)carbonyl)amino)-1-((tert-butoxy)carbonyl)pyrrolidine-2-carboxylic acidHCID 536486284-Fluorophenoxyaniline

生成物 1

HCID 67009501(2S,4R)-tert-butyl 4-(benzyloxycarbonylamino)-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Step (b) A flask was charged with (2S,4R)-4-(benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (2.51 g, 6.86 mmol), HATU (2.87 g, 7.55 mmol), 4-fluorophenoxyaniline (1.41 g, 6.86 mmol), DIEA (5.0 mL, 29 mmol) and DMF (20 mL). The reaction mixture was stirred at ambient temperature for 30 minutes and then quenched with saturated sodium bicarbonate (aq., 20 mL). The mixture was extracted with ethyl acetate (60 mL) and the extract was washed with deionized water (30 mL) and then brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give (2S,4R)-tert-butyl 4-(benzyloxycarbonylamino)-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate as a crude mixture which was carried forward without further purification.

後処理

  1. customquenched with saturated sodium bicarbonate (aq., 20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (60 mL)
  3. washthe extract was washed with deionized water (30 mL)
  4. dry with materialbrine (30 mL), dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-4c160b8468ce4d93ab463d31c4994136
出典データセット
uspto-grants-2014_07
特許番号
US08791102B2

反応ノート

読み込み中…