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

HRID 1630080노트

반응식

HRID 1630080 반응식
[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

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4c160b8468ce4d93ab463d31c4994136
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791102B2

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