Hydrochloric Acid → benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate

HRID 25693Notes

Reaction equation

HRID 25693 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][NH:7][C:8](=[O:22])[C@@H:9]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:10])C.Cl>O1CCCC1>[CH3:10][C@H:9]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:8](=[O:22])[NH:7][CH2:6][CH2:5][CH:4]=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59065857benzyl (1S)-2-[(3,3-diethoxypropyl)amino]-1-methyl-2-oxoethylcarbamate

Product 1

HCID 59065906benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamateYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 14, benzyl (1S)-2-[(3,3-diethoxypropyl)amino]-1-methyl-2-oxoethylcarbamate (2.39 g, 6.79 mmol, obtained from Reference Example 19) in tetrahydrofuran (14 ml) was reacted with 0.5 N hydrochloric acid (14 ml) for 45 minutes, to provide benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate (1.92 g, 100%) as a pale yellow waxy solid.

Sources & evidence

ORD record
ord-0dbdbe3d0b974bb0bf9ada78178ffe22
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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