Hydrochloric Acid → HCID 68420297, compound

HRID 20243Notes

Reaction equation

HRID 20243 reaction equation
Cl.[NH2:2][C:3](=[O:30])[CH2:4][CH2:5][N:6]([C:23](OC(C)(C)C)=[O:24])[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1>C(OCC)(=O)C>[O:24]=[C:23]1[NH:2][C:3](=[O:30])[CH2:4][CH2:5][N:6]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68425948Benzyl 4-[(3-amino-3-oxopropyl)(tert-butoxycarbonyl)amino]piperidin-1-carboxylate

Product 1

HCID 68420297HCID 68420297, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4N Hydrogen chloride in ethyl acetate (4 mL) was added to a solution of benzyl 4-[(3-amino-3-oxopropyl)(tert-butoxycarbonyl)amino]piperidin-1-carboxylate (3.38 g) obtained in Example 45c) in ethyl acetate (16 mL), and the mixture was stirred at room temperature for 15 hours. The white solid (2.73 g) formed was collected by filtration. A solution of the resulting white solid (1.0 g), CDI (0.47 g) and DBU (0.89 g) in dichloroethane (30 mL) was refluxed for 15 hours. The reaction mixture was washed with an aqueous 5% citric acid solution and saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (0.21 g, 21%) as a white powder.

Sources & evidence

ORD record
ord-9dd578aff7094bc785b5fdc099f805a3
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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