Ethylmorpholine → HCID 86761448, compound

HRID 655202Notes

Reaction equation

HRID 655202 reaction equation
[CH:1]([N:3](C1C=CC(F)=CC=1)[CH2:4][C:5]([OH:7])=O)=[O:2].CO[C:17]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][CH2:20][NH2:21].C(N1C[CH2:34][O:33]CC1)C.CN(C(ON1N=N[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]1=2)=[N+](C)C)C.[B-](F)(F)(F)[F:54]>CN(C=O)C>[CH3:27][O:26][C:25]1[CH:17]=[C:18]([CH2:19][CH2:20][NH:21][C:5](=[O:7])[CH:4]([C:45]2[CH:46]=[CH:47][C:48]([F:54])=[CH:49][CH:50]=2)[NH:3][CH:1]=[O:2])[CH:22]=[CH:23][C:24]=1[O:33][CH3:34]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 1378582,3-DimethoxyphenethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86761449HCID 86761449, compound

Product 1

HCID 86761448HCID 86761448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-formyl-4-fluorophenylglycine (900 mg) and 2,3-dimethoxyphenethylamine (1 ml) in DMF (5 ml) was added N-ethylmorpholine (0.75 ml) and TBTU (1.6 g). After stirring for 4 h, the reaction was quenched by addition of water (30 ml). The product was extracted with ethylacetate. The organic layer was washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with methyl-tert.butylether and recrystallized from toluene.

Workup

  1. customthe reaction was quenched by addition of water (30 ml)
  2. extractionThe product was extracted with ethylacetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with methyl-tert.butylether
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e1a2af46a098420786f22507da9aabc3
Source dataset
uspto-grants-2011_12
Patent number
US08071587B2

Reaction notes

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