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Sodium Bicarbonate → Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate

HRID 43668
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HRID 43668 반응식
[C:1]([N:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:6]([O:21][CH2:22][CH3:23])[CH2:5]1)(=[O:3])[NH2:2].Br[CH:25]([CH2:35][CH3:36])[C:26](=O)[C:27]([O:29][CH2:30][CH2:31]CC)=[O:28].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:13]([O:12][C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][N:4]([C:1]2[O:3][C:25]([CH2:35][CH3:36])=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:2]=2)[CH2:5][C@H:6]1[O:21][CH2:22][CH3:23])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 86648534Butyl 3-bromo-2-oxopentanoateHCID 131730865cis(+/-)-Benzyl (1-carbamoyl-3-ethoxypiperidin-4-yl)carbamate

생성물 1

HCID 117815261Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate수율 90.5%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-ethoxypiperidin-4-yl)carbamate obtained in Example (112f) (0.95 g, 3 mmol), butyl 3-bromo-2-oxopentanoate obtained in Example (106a) (5 g, 19.9 mmol), sodium bicarbonate (0.72 g, 9 mmol) and THF (15 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1) to obtain 1.21 g of the title compound as a light yellow oily substance (86%).

후처리

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1)

출처 및 근거

ORD 기록
ord-f023e66e1622458fa22c49b15e971e30
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536197B2

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