4-Methylmorpholine → HCID 59119733, compound

HRID 434139Notes

Reaction equation

HRID 434139 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].CN1CCOCC1.[C:22]([N:33]1[C@@H:37]([CH3:38])[C:36](=O)[O:35]C1=O)(=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:36](=[O:35])[C@H:37]([CH3:38])[NH:33][C:22](=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 59119737HCID 59119737, compound

Product 1

HCID 59119733HCID 59119733, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

L-Phenylalanine methyl ester hydrochloride (259 mg, 1.2 mmol) was suspended in tetrahydrofuran (6 mL), followed by the addition of N-methylmorpholine (121 mg, 1.2 mmol) at 0° C. The resulting mixture was stirred for 20 minutes. (S)-3-Decanoyl-4-methyl-2,5-oxazolidinedione (N-decanoyl-L-alanine-NCA) (270 mg, 1 mmol) was added as crystals at 0° C., followed by stirring for 5 minutes. The mixture was allowed to rise in temperature to room temperature, at which the mixture was stirred for 30 minutes. The reaction mixture was treated in a similar manner as in Example 19 to afford the title compound (289 mg, 71%) as white crystals.

Workup

  1. stirringby stirring for 5 minutes
  2. customto rise in temperature to room temperature, at which
  3. stirringwas stirred for 30 minutes
  4. additionThe reaction mixture was treated in a similar manner as in Example 19

Sources & evidence

ORD record
ord-b6497e83926942af90b93c4b7e6ce10d
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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