4-Methylmorpholine → HCID 54083819, compound

HRID 2119108Notes

Reaction equation

HRID 2119108 reaction equation
[CH3:1][CH:2]([CH3:10])[CH2:3][C:4](=[CH:8][CH3:9])[C:5]([OH:7])=O.[CH3:11]N1CCOCC1.C(Cl)(=O)C(Cl)=O.[CH3:24][NH:25][C:26](=[O:38])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:31]=1C)[NH2:28]>ClCCl>[CH3:24][NH:25][C:26](=[O:38])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:11])=[CH:32][CH:31]=1)[NH:28][C:5](=[O:7])[C:4]([CH2:3][CH:2]([CH3:1])[CH3:10])=[CH:8][CH3:9]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 65578Oxalyl chlorideHCID 53446042HCID 53446042, compoundHCID 69967479HCID 69967479, compound

Product 1

HCID 54083819HCID 54083819, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-(2-Methylpropyl)-but-2-enoic acid (37 g, 0.261 M) prepared as described in Example 1 in dry dichloromethane (200 ml) and N-methyl morpholine (65 ml) was treated at -5° C. with oxalyl chloride (33.2 g, 0.261 M) over 30 minutes. The mixture was heated under reflux for 10 minutes, then re-cooled to ca -60° C. and 0-methyl-L-tyrosine N-methylamide (51 g, 0.245 M) in dry dichloromethane (100 ml) added over 30 minutes. The mixture was left to warm up to room temperature over ca 1 hour, diluted with more dichloromethane then washed with aqueous sodium hydroxide (0.1 N), aqueous saturated sodium hydrogen carbonate solution and saturated brine. The organic extract was dried, then evaporated in vacuo to afford N-[2-(2-methylpropyl)-but-2-enoyl]-O-methyl-L-tyrosine-N-methylamide as a yellow gum (81 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturere-cooled to ca -60° C.
  4. waitThe mixture was left
  5. washthen washed with aqueous sodium hydroxide (0.1 N), aqueous saturated sodium hydrogen carbonate solution and saturated brine
  6. extractionThe organic extract
  7. customwas dried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b5ffc5bf205f4f97bc16b5899e15280d
Source dataset
uspto-grants-1987_07
Patent number
US04681966

Reaction notes

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