Hydrochloric Acid → [(1S,2S)-2-hydroxy-1-(3-oxo-propylcarbamoyl)-propyl]-carbamic acid benzyl ester

HRID 25691

Reaction equation

HRID 25691 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]([C:15](=[O:26])[NH:16][CH2:17][CH2:18][CH:19](OCC)[O:20]CC)[C@@H:12]([OH:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]([C:15](=[O:26])[NH:16][CH2:17][CH2:18][CH:19]=[O:20])[C@@H:12]([OH:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69752191[(1S,2S)-1-(3,3-diethoxy-propylcarbamoyl)-2-hydroxy-propyl]-carbamic acid benzyl ester

Product 1

HCID 86587933[(1S,2S)-2-hydroxy-1-(3-oxo-propylcarbamoyl)-propyl]-carbamic acid benzyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 14, [(1S,2S)-1-(3,3-diethoxy-propylcarbamoyl)-2-hydroxy-propyl]-carbamic acid benzyl ester (2 g, 5.24 mmol, obtained from Reference Example 17) in tetrahydrofuran (10 ml) was reacted with 0.5 N hydrochloric acid (10 ml) for 30 minutes at room temperature, to provide [(1S,2S)-2-hydroxy-1-(3-oxo-propylcarbamoyl)-propyl]-carbamic acid benzyl ester (1.56 g, 97%) as a white solid.

Sources & evidence

ORD record
ord-6a414f839a2249c08e81844597337c20
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Linked notes

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