Morpholine → (2-Morpholin-4-yl-2-oxo-1-phenylethyl)carbamic acid tert-butyl ester

HRID 645492

Reaction equation

HRID 645492 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CCN=C=NCCCN(C)C.Cl.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 87672115EDCl H2O

Product 1

HCID 68708152(2-Morpholin-4-yl-2-oxo-1-phenylethyl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butoxycarbonylaminophenylacetic acid (4.0 mmol) in CH2Cl2 (8.0 mL) is added morpholine (4.0 mmol), EDCl—H2O (4.8 mmol) and DMAP (0.40 mmol) at room temperature. After stirring at room temperature for 24 h, the reaction is quenched by the addition of water. The mixture is extracted with AcOEt. The combined organic extracts are washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting solid is triturated with ether-n-hexane to give the title compound; 1H NMR (CDCl3) δ 1.41 (s, 9H), 3.08-3.12 (m, 1H), 3.20-3.28 (m, 1H), 3.39-3.45 (m, 1H), 3.49-3.60 (m, 3H), 3.66-3.76 (m, 2H), 5.54 (d, 1H), 6.01 (d, 1H), 7.29-7.36 (m, 5H).

Workup

  1. customthe reaction is quenched by the addition of water
  2. extractionThe mixture is extracted with AcOEt
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid is triturated with ether-n-hexane

Sources & evidence

ORD record
ord-a82ea35a0aca46be9699086903d53452
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Linked notes

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