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

HRID 1425092Notes

Reaction equation

HRID 1425092 reaction equation
[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]([CH3:34])[C:25](=O)[C:26]([O:28][CH2:29][CH2:30]CC)=[O:27].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:24]([CH3:34])=[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

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 87440690Butyl 3-bromo-2-oxobutanoateHCID 131730860cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

Product 1

HCID 131730861Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-oxazole-4-carboxylateYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (1.97 g, 6.4 mmol), butyl 3-bromo-2-oxobutanoate obtained in Example (106a) (10 g, 42.3 mmol), sodium bicarbonate (1.26 g, 15 mmol) and THF (40 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 2.09 g of the title compound as a yellow oily substance (73%).

Workup

  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)

Sources & evidence

ORD record
ord-3d1178fa451643feb57a13f2a8585e34
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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