4-Methylmorpholine → HCID 86754075, compound

HRID 1075677Notes

Reaction equation

HRID 1075677 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2.C(OC([NH:31][C@H:32]([C:34](O)=[O:35])[CH3:33])=O)(C)(C)C.CN1CCOCC1>C1COCC1>[NH2:31][C@H:32]([C:34]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2)=[O:35])[CH3:33]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 54035407HCID 54035407, compound

Product 1

HCID 86754075HCID 86754075, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-3-(8-hydroxyquinol-5-ylmethylen)-2-oxindole (497 mg, 1.64 mmol) and of t-butoxycarbonyl-L-alanine (360 mg, 1.9 mmol in 80 ml of THF were added 950 mg (1.82 mmol) of benzotriazol-1-yloxytripyrrolidinophosphoniun hexafluorophosphate and 0.2 ml (1.87 mmol) of N-methylmorpholine. The reaction was maintained at room temperature for 4 h. After evaporation of the solvent the residue was purified by flash chromatography with cyclohexane/ethyl acetate 3:7. The evaporated eluant was solubilized in dichloromethane, 10 ml of trifluoroacetic acid was added and the mixture stirred at room temperature for 1 h. After the usual workup pure title compound was obtained in 80% yield (491 mg).

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas purified by flash chromatography with cyclohexane/ethyl acetate 3:7
  3. addition10 ml of trifluoroacetic acid was added

Sources & evidence

ORD record
ord-f4bbe779f3dd4a23a791a49588c33305
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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