Morpholine → tert-butoxycarbonyl-(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine

HRID 44651

Reaction equation

HRID 44651 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([CH3:10])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 13678038(S)-2-(Boc-amino)-2-phenylpropanoic acid

Product 1

HCID 57444165tert-butoxycarbonyl-(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamineYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

630 mg (2.374 mmol) of N-(tert-butoxycarbonyl)-2-phenyl-D-alanine were dissolved in 20 mL of dry DMF and O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoborate (TBTU, 1.37 g, 4.27 mmol), morpholine (0.412 mL, 4.73 mmol) and diisopropylethylamine (1.63 mL, 9.5 mol) were added. The mixture was stirred at room temperature for 1 hour, then the solvent was removed and the residue dissolved with dichloromethane. The solution was washed with saturated NaHCO3, brine, water and dried over Na2SO4. 700 mg of the title compound were recovered (88% yield).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved with dichloromethane
  3. washThe solution was washed with saturated NaHCO3, brine, water
  4. dry with materialdried over Na2SO4
  5. custom700 mg of the title compound were recovered (88% yield)

Sources & evidence

ORD record
ord-b8729780c0e546f6bf715a96e00cab8d
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Linked notes

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