4-Methylmorpholine → 1-[3-(triphenylmethylthio)-2-methylpropanoyl]-L-proline

HRID 262578Notes

Reaction equation

HRID 262578 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:8][CH2:9][CH:10]([CH3:14])[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30].CN1CCOCC1>O1CCCC1.CC(N(C)C)=O>[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[S:8][CH2:9][CH:10]([CH3:14])[C:11]([N:27]2[CH2:34][CH2:33][CH2:32][C@H:28]2[C:29]([OH:31])=[O:30])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 145742L-ProlineHCID 213191543-Triphenylmethylthio-2-methylpropanoic acid

Product 1

HCID 544430751-[3-(triphenylmethylthio)-2-methylpropanoyl]-L-proline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

3-Triphenylmethylthio-2-methylpropanoic acid (1.8 g.) and N,N'-carbonyldiimidazole (0.8 g.) are dissolved in tetrahydrofuran (10 ml.) with stirring at room temperature. After twenty minutes, the solution is added to a mixture of L-proline (0.6 g.) and N-methylmorpholine (1 g.) in dimethylacetamide (20 ml.). The resulting mixture is stirred overnight at room temperature, concentrated to dryness and the residue dissolved in a mixture of ethyl acetate and 10% aqueous potassium bisulfate. The organic layer is separated and dried and concentrated to dryness in vacuo to obtain 1-[3-(triphenylmethylthio)-2-methylpropanoyl]-L-proline. Rf :=0.4 (Silica gel, Benzene/acetic acid 3:1), Rf 1.0 (Silica gel, Methyl-ethylketone/acetic acid/pyridine/water 14:1:2:1).

Workup

  1. waitAfter twenty minutes
  2. stirringThe resulting mixture is stirred overnight at room temperature
  3. concentrationconcentrated to dryness
  4. dissolutionthe residue dissolved in a mixture of ethyl acetate and 10% aqueous potassium bisulfate
  5. customThe organic layer is separated
  6. customdried
  7. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-0dcaf26feb994f5db5c9cabb3078a35f
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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