4-Methylmorpholine → HCID 178451297, compound

HRID 325600Notes

Reaction equation

HRID 325600 reaction equation
Cl.[CH3:2][C:3]([O:6][C:7](=[O:22])[CH2:8][NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)([CH3:5])[CH3:4].CN1CCOCC1.[C:30]([S:38][CH2:39][CH2:40][C:41](Cl)=[O:42])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:5][C:3]([O:6][C:7](=[O:22])[CH2:8][N:9]([C:41](=[O:42])[CH2:40][CH2:39][S:38][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH2:15]1)([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 13013918S-benzoyl-3-mercaptopropanoyl chlorideHCID 178451269HCID 178451269, compound

Product 1

HCID 178451297HCID 178451297, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the compound of Example I (0.60 g, 0.0018 mole) and CH2Cl2 (6 ml) was added N-methylmorpholine (0.44 g, 0.0043 mole). The resulting mixture was cooled on an ice bath and 3-benzoylthiopropanoyl chloride (0.45 g, 0.0020 mole) was added dropwise. After stirring 10 min the mixture was filtered removing the insolubles. The CH2Cl2 solution was washed with 20% citric acid, H2O, 10% NaHCO3, H2O and dried over MgSO4. The filtered solution was concentrated under reduced pressure to dryness and then azeotroped with diethyl ether to a semi-solid residue. This residue was dissolved in a small amount of diethyl ether and precipitated with hexane to give a crystalline solid. Drying in vacuo at 60° overnight gave 0.48 g (0.001 mole, 55%) of trans-N-(3-benzoylthio-1-oxopropyl)-N-(4-phenylcyclohexyl)glycine-1,1-dimethylethyl ester.

Workup

  1. temperatureThe resulting mixture was cooled on an ice bath
  2. filtrationwas filtered
  3. customremoving the insolubles
  4. washThe CH2Cl2 solution was washed with 20% citric acid, H2O, 10% NaHCO3, H2O
  5. dry with materialdried over MgSO4
  6. concentrationThe filtered solution was concentrated under reduced pressure to dryness
  7. customazeotroped with diethyl ether to a semi-solid residue
  8. dissolutionThis residue was dissolved in a small amount of diethyl ether
  9. customprecipitated with hexane
  10. customto give a crystalline solid
  11. customDrying in vacuo at 60° overnight

Sources & evidence

ORD record
ord-b5022f2345484439990244972667ab5d
Source dataset
uspto-grants-1984_04
Patent number
US04442038

Reaction notes

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