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

HRID 2197662
Notes
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Reaction equation

HRID 2197662 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 23365gamma-Aminobutyric acid ethyl esterHCID 86617530methanesulfonic acid (R)-1-carbamoyl-propyl ester

Product 1

HCID 54059837ethyl-(R)-4-(1-carbamoylpropylamino)butyrate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. filtrationThe mixture is then filtered
  2. washthe cake rinsed with acetonitrile (50 ml)
  3. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes