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

HRID 2197664
Notes
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Reaction equation

HRID 2197664 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23365gamma-Aminobutyric acid ethyl esterHCID 86617530methanesulfonic acid (R)-1-carbamoyl-propyl ester

Product 1

HCID 29938336ethyl (S)-4-[[1-(aminocarbonyl)propyl]amino]butyrate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. filtrationThe mixture is then filtered
  2. washthe cake rinsed with acetonitrile (30 ml)
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes