Diisopropylethylamine → Benzyl 4-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethoxy)piperidine-1-carboxylate

HRID 1091768노트

반응식

HRID 1091768 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([OH:21])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[F:23][C:24]1([F:28])[CH2:27][NH:26][CH2:25]1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:23][C:24]1([F:28])[CH2:27][N:26]([C:19](=[O:21])[CH2:18][O:17][CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)[CH2:25]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 189194942-((1-((Benzyloxy)carbonyl)piperidin-4-YL)oxy)acetic acid

생성물 1

HCID 57791852Benzyl 4-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethoxy)piperidine-1-carboxylate수율 65.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(1-(Benzyloxycarbonyl)piperidin-4-yloxy)acetic acid (4.12 g, 14.05 mmol), 3,3-difluoroazetidine hydrochloride (1.4 g, 10.81 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (3.47 g, 10.81 mmol) were dissolved in DMF (50 mL), to this was added DIPEA (4.91 mL, 28.10 mmol) and the reaction was stirred overnight. The solvent was evaporated and the reaction mixture was quenched with 2M NaOH (50 mL), extracted with Et2O (3×50 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired material as a yellow gum (2.59 g, 65.1% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.67-1.49 (2H, m), 1.90-1.81 (2H, m), 3.26-3.19 (2H, m), 3.58-3.51 (1H, m), 3.84-3.78 (2H, m), 4.13 (2H, s), 4.36 (2H, t), 4.60 (2H, t), 5.12 (2H, s), 7.40-7.29 (5H, m).

후처리

  1. customThe solvent was evaporated
  2. customthe reaction mixture was quenched with 2M NaOH (50 mL)
  3. extractionextracted with Et2O (3×50 mL)
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-c5241508481e43e68484c1344ce4bb3e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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