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

HRID 43643
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HRID 43643 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][CH3:22])[CH2:5]1)(=[O:3])[NH2:2].Br[CH:24]([CH2:34][CH3:35])[C:25](=O)[C:26]([O:28][CH2:29][CH2:30]CC)=[O:27].[C:36](=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:24]([CH:34]([CH3:35])[CH3:36])=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:2]=2)[CH2:5][C@H:6]1[O:21][CH3:22])=[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 131730860cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

생성물 1

HCID 131730863Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-isopropyl-1,3-oxazole-4-carboxylate수율 100%

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-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (0.97 g, 3.16 mmol), butyl 3-bromo-4-methyl-2-oxobutanoate obtained in Example (111a) (7.6 g, 30.2 mmol), sodium bicarbonate (0.7 g, 8.3 mmol) and THF (20 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 2/3, 1/1, 3/2, 2/1) to obtain 0.43 g of the title compound as a colorless solid (100%).

후처리

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 2/3, 1/1, 3/2, 2/1)

출처 및 근거

ORD 기록
ord-04cc79037f6f422aba0152b284017860
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536197B2

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