Potassium Carbonate → ethyl (S)-4-[[1-(aminocarbonyl)propyl]amino]butyrate

HRID 2197664Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[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: 80 °C

Procedure

A mixture of powdered potassium carbonate (14.0 g, 96.2 mmol, 5 equiv.), ethyl-4-aminobutyrate (IVb) (6.5 g, 38.6 mmol, 2 equiv.) and methanesulfonic acid (R)-1-carbamoyl-propyl ester (IIi) (3.5 g, 19.3 mmol, 1 equiv.) in acetonitrile (40 ml, 11 vol.) is heated to 80° C. for 17 hours. The mixture is then filtered and the cake rinsed with acetonitrile (30 ml). Combined filtrates are concentrated to dryness under reduced pressure. The crude methyl-(S)-4-(1-carbamoylpropylamino)butyrate (VIg) obtained as a yellow oil is used directly in the next step.

Workup

filtrationThe mixture is then filtered
washthe cake rinsed with acetonitrile (30 ml)
concentrationCombined filtrates are concentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-72c363b4584a4c4282ee76fa16dcfa0e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338621B2

Reaction notes

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