4-Methylmorpholine → HCID 53957133, compound

HRID 1369271Notes

Reaction equation

HRID 1369271 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:14][C:15](=[O:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8](Br)[CH:7]=1.[P:19]([O-:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].CN1CCOCC1>C1(C)C=CC=CC=1.CC#N.[NH4+].[Cl-]>[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:14][C:15](=[O:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([P:19]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:26])[CH:7]=1

Participants

7

Reactant 3

HCID 79724-MethylmorpholineHCID 3780918DiethylphosphiteHCID 54126761HCID 54126761, compound

Product 1

HCID 53957133HCID 53957133, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To 2-Acetylamino-3-(3-bromo-4-hydroxy-phenyl)-propionic acid methyl ester (3 g, 9 mmol), diethyl phosphite (1.6 ml, 11 mmol) and 4-methylmorpholine (1.5 mL, 13.5 mmol) in toluene (10 mL) and MeCN (10 mL) was added Pd(Ph3)4 (0.5 g, 0.45 mmol). The mixture was allowed to stir for two days at 100° C. It was then diluted with saturated NH4Cl and extracted with EtOAc. The organic layer was dried over magnesium sulfate, concentrated , and chromatographed over silica gel (5% MeOH/CHCl3) to an oil. MS [M+H]+ 374 and [M−H]− 372.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customchromatographed over silica gel (5% MeOH/CHCl3) to an oil

Sources & evidence

ORD record
ord-49a9193e82bb4450b843b09d1f56ad95
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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