Cesium carbonate → ethyl-(R)-4-(1-carbamoylpropylamino)butyrate

HRID 2197662Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][NH2:14])[CH3:8].[C:16]([C@H:19](OS(C)(=O)=O)[CH2:20][CH3:21])(=[O:18])[NH2:17]>C(#N)C>[CH2:7]([O:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][NH:14][C@@H:19]([C:16](=[O:18])[NH2:17])[CH2:20][CH3:21])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of powdered caesium carbonate (9.0 g, 27.4 mmol, 5 equiv.), ethyl-4-aminobutyrate (IVb) (1.85 g, 11.0 mmol, 2 equiv.) and methanesulfonic acid (R)-1-carbamoyl-propyl ester (IIi) (1.0 g, 5.5 mmol, 1 equiv.) in acetonitrile (20 ml, 20 vol.) is heated to 60° C. for 16 hours. The mixture is then filtered and the cake rinsed with acetonitrile (50 ml). Combined filtrates are concentrated to dryness under reducd pressure. The crude methyl-(R)-4-(1-carbamoylpropylamino)butyrate is used directly in the next step.

Workup

filtrationThe mixture is then filtered
washthe cake rinsed with acetonitrile (50 ml)
concentrationCombined filtrates are concentrated to dryness under reducd pressure

Sources & evidence

ORD record: ord-d6dace805175480cba2f21e509d3e6ba
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338621B2

Reaction notes

Loading…