Methyl chloroformate → HCID 66611160, compound

HRID 76206Notes

Reaction equation

HRID 76206 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([NH2:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[Na+].[Na+].Cl[C:28]([O:30][CH3:31])=[O:29]>CC(C)=O>[CH3:31][O:30][C:28](=[O:29])[NH:20][CH:18]([C:15]1[CH:14]=[CH:13][C:12]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:17][CH:16]=1)[CH3:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 666103261-(4-((4-Ethoxyphenyl)ethynyl)phenyl)ethanamine

Product 1

HCID 66611160HCID 66611160, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To 26.5 mg (0.10 mmol) 1-[4-(4-ethoxy-phenylethynyl)-phenyl]-ethylamine (I63) in 2.00 mL acetone are added 47.7 mg (0.45 mmol) Na2CO3 and 10.2 μL methyl chloroformate. The reaction mixture is stirred at 40° C. for 3 h. After cooling down to r.t. the reaction mixture is filtered and the solvent is removed in vacuo. The residue is purified by HPLC (MeOH/H2O/TFA).

Workup

  1. temperatureAfter cooling down to r.t. the reaction mixture
  2. filtrationis filtered
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-87bf132310614ab08924459b9b605cf9
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

Loading…