N-Benzylglycine ethyl ester → HCID 57751914, compound

HRID 1967412Notes

Reaction equation

HRID 1967412 reaction equation
B(O)(O)[C@H]1N(C([C@@H](N)C(C)C)=O)CCC1.CS(O)(=O)=O.[CH3:21][O:22][C:23](=[O:30])[CH2:24][C@H:25]([CH2:28][F:29])[CH2:26]Br.[CH2:31]([O:33][C:34](=[O:44])[CH2:35][NH:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:32]>C(#N)C>[CH3:21][O:22][C:23](=[O:30])[CH2:24][C@H:25]([CH2:28][F:29])[CH2:26][N:36]([CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:44]

Participants

5

Reactant 3

HCID 80908N-Benzylglycine ethyl esterHCID 11522448Talabostat mesylateHCID 57751913HCID 57751913, compound

Product 1

HCID 57751914HCID 57751914, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 2.5-1 four-necked flask equipped with a mechanical stirrer, a reflux condenser, a Pt-100 thermometer, and an argon in/outlet, bromide 2 (110 g, 519 mmol) was dissolved in acetonitrile (880 ml). To this solution was added N-benzylglycine ethyl ester (256 g, 1.30 mol) and the reaction mixture was refluxed for 71 hours, slowly turning dark red during this time. After cooling to room temperature, the mixture was concentrated under reduced pressure. The dark red oil was filtered over silica gel (800 g) using EtOAc:heptane 1:9 as eluent, giving the crude title compound 3 (169 g) as yellow oil which was used without further purification.

Workup

  1. customIn a 2.5-1 four-necked flask equipped with a mechanical stirrer, a reflux condenser
  2. temperaturethe reaction mixture was refluxed for 71 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. filtrationThe dark red oil was filtered over silica gel (800 g)

Sources & evidence

ORD record
ord-3ce81143290b4a30ab1d740dbbae4db9
Source dataset
uspto-grants-2013_04
Patent number
US08420818B2

Reaction notes

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