Hydrochloric Acid → [(1S)-3-methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl ester

HRID 25690Notes

Reaction equation

HRID 25690 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@H:11]([C:16](=[O:27])[NH:17][CH2:18][CH2:19][CH:20](OCC)[O:21]CC)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@H:11]([C:16](=[O:27])[NH:17][CH2:18][CH2:19][CH:20]=[O:21])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59065878HCID 59065878, compound

Product 1

HCID 44366907[(1S)-3-methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl esterYield 113.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 14, [(1S)-1-(3,3-diethoxy-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester (1.0 g, 2.5 mmol, obtained from Reference Example 15) in tetrahydrofuran was reacted with 0.5N hydrochloric acid (5 mL) for 15 min, to provide [(1S)-3-methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl ester (906 mg, 100%) as a white solid.

Sources & evidence

ORD record
ord-92bc5a10842f416aae22094bb8e9448f
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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