Ethylmorpholine → HCID 58031811, compound

HRID 240260Notes

Reaction equation

HRID 240260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(N1CCOCC1)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.[CH:48]([C:51]1[CH:52]=[C:53]([CH:60]=[CH:61][CH:62]=1)[O:54][CH:55]([CH3:59])[C:56](O)=[O:57])([CH3:50])[CH3:49]>CN(C=O)C.O>[CH:48]([C:51]1[CH:52]=[C:53]([CH:60]=[CH:61][CH:62]=1)[O:54][CH:55]([CH3:59])[C:56]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1)=[O:57])([CH3:49])[CH3:50]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 162280102-[3-(1-Methylethyl)phenoxy]propanoic acidHCID 66628746HCID 66628746, compound

Product 1

HCID 58031811HCID 58031811, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 200 mg (0.75 mmol) of ethyl 3-(4-aminophenyl)hex-4-ynoate, 258 mg (2.24 mmol) of N-ethylmorpholine, 126 mg (0.82 mmol) of HOBt hydrate and 128 mg (0.82 mmol) of EDAC in 3 ml of DMF was added a solution of 202 mg (0.74 mmol) of 2-(3-isopropylphenoxy)propionic acid in 2.5 ml of DMF. After 72 h at room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. This gave 156 mg of ethyl 3-{4-[2-(3-isopropylphenoxy)propionylamino]phenyl}hex-4-ynoate.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b50651cfbb3474c884d60525e4e15c5
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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