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

HRID 1425137노트

반응식

HRID 1425137 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][CH2:23][CH3:24])[CH2:5]1)(=[O:3])[NH2:2].Br[CH:26]([CH2:36][CH3:37])[C:27](=O)[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:29].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:26]([CH2:36][CH3:37])=[C:27]([C:28]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:29])[N:2]=2)[CH2:5][C@H:6]1[O:21][CH2:22][CH2:23][CH3:24])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 86648534Butyl 3-bromo-2-oxopentanoateHCID 131730866HCID 131730866, 화합물

생성물 1

HCID 86648605Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate수율 86.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-propoxypiperidin-4-yl)carbamate obtained in Example (113f) (0.80 g, 2.39 mmol), butyl 3-bromo-2-oxopentanoate obtained in Example (110a) (4 g, 15.9 mmol), sodium bicarbonate (0.7 g, 8.33 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 1.01 g of the title compound as a light brown oily substance (87%).

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-9a5a7795bee54addb2d9a8467aa92fc9
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927588B2

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