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

HRID 25695Notes

Reaction equation

HRID 25695 reaction equation
[CH2:1]([C@H:8]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][CH:14](OCC)[O:15]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([C@H:8]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH:14]=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59065908benzyl (1S)-1-benzyl-2-[(3,3-diethoxypropyl)amino]-2-oxoethylcarbamate

Product 1

HCID 59065893benzyl (1S)-1-benzyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 14, 1-benzyl-2-[(3,3-diethoxypropyl)amino]-2-oxoethylcarbamate (2.37 g, 5.54 mmol, obtained from Reference Example 21) in tetrahydrofuran (11 ml) was reacted with 0.5 N hydrochloric acid (11 ml) for 45 minutes at room temperature, to provide benzyl (1S)-1-benzyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate (1.84 g, 94%) as a white solid.

Sources & evidence

ORD record
ord-997fd63724e74490b109c229670c0317
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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