4-Methylmorpholine → HCID 20610777, compound

HRID 434140Notes

Reaction equation

HRID 434140 reaction equation
[C:1]([N:12]1[C@@H:16]([CH3:17])[C:15](=[O:18])OC1=O)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:20]1([CH3:29])[CH:25]=[CH:24][C:23]([C@@H:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=1.CN1CCOCC1>O1CCCC1>[C:20]1([CH3:29])[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:15](=[O:18])[C@H:16]([CH3:17])[NH:12][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 7015759(S)-1-(p-tolyl)ethanamineHCID 59119737HCID 59119737, compound

Product 1

HCID 20610777HCID 20610777, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-Decanoyl-4-methyl-2,5-oxazolidinedione (N-decanoyl-L-alanine-NCA) (100 mg, 0.37 mmol) was dissolved in tetrahydrofuran (3 mL), and at 0° C., (S)-1-(p-tolyl)ethylamine (49 mg, 0.36 mmol) and N-methylmorpholine (37 mg, 0.36 mmol) were added, followed by stirring for 30 minutes. The reaction mixture was treated in a similar manner as in Example 19 to afford the title compound (103 mg, 77%) as white crystals.

Workup

  1. additionThe reaction mixture was treated in a similar manner as in Example 19

Sources & evidence

ORD record
ord-ff9a37867cfe4921a44facf0b2b59abc
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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