4-Methylmorpholine → HCID 57835791, compound

HRID 1160331Notes

Reaction equation

HRID 1160331 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-ca7ca112a02c45778c1dfb0d438e4487
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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