4-Methylmorpholine → HCID 57835791, compound

HRID 1993080Notes

Reaction equation

HRID 1993080 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:20](C)[CH2:21][CH2:22][CH2:23]N=C=NCC.C(N)C#C.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH:20][CH2:21][C:22]#[CH:23])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 810334-Benzyloxyphenylacetic acidHCID 239041Propargylamine

Product 1

HCID 57835791HCID 57835791, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(benzyloxy)phenylacetic acid (20.7 mmol), 1-hydroxybenzotrizole hydrate (37 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (37 mmol), propargylamine (20.7 mmol) and N-methylmorpholine (62 mmol) in DMF (60 mL) were stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (400 mL), washed with 1N HCl, water, saturated Na2CO3 solution, brine and dried over Na2SO4. After removing solvent under reduced pressure, the residue was triturated with dichloromethane. Compound 60.1 was obtained as a white solid after filtration and drying. LC-MS ESI (pos.) m/e: 280 (M+H).

Workup

  1. washwashed with 1N HCl, water, saturated Na2CO3 solution, brine
  2. dry with materialdried over Na2SO4
  3. customAfter removing solvent under reduced pressure
  4. customthe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-05c84507c30b44e8a0164035a15f96bc
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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