Ethyl chloroformate → HCID 69584952, compound

HRID 2212445Notes

Reaction equation

HRID 2212445 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:15][NH:16]C(OC(C)(C)C)=O)([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([OH:13])[CH:7]=1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>ClCCl>[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:15][NH2:16])([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:8]([OH:13])[CH:7]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 69584993HCID 69584993, compound

Product 1

HCID 69584952HCID 69584952, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold reaction mixture containing compound 108 (0.17 g, 0.5 mmol) and TEA (0.07 mL, 0.5 mmol) in dichloromethane (5 mL) was added ethyl chloroformate (0.025 mL, 0.5 mmol). The resulting mixture was stirred at 0° C. for 30 min and then at room temperature for 1. After concentration, the residue was partitioned with 10% citric acid and ethyl acetate. The organic phase was separated and dried over MgSO4. After removing the solvent under reduced pressure, the resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min. Removal of the solvent and purification by reverse phase preparative HPLC afford 73 mg of a 1:1 mixture of the title compounds 123 and 124. 1H NMR (CD3OD, 400 MHz): 1.35 (q, 3H), 1.46 (d, 3H), 2.98 (dd, 2H), 3.80 (d, 3H), 4.28 (q, 4H), 6.60–6.98 (m, 3H). MS (ESI) m/z 313.25 (M+H+).

Workup

  1. customat room temperature
  2. concentrationAfter concentration
  3. customthe residue was partitioned with 10% citric acid and ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. customAfter removing the solvent under reduced pressure
  7. additionthe resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min
  8. customRemoval of the solvent and purification by reverse phase preparative HPLC
  9. customafford

Sources & evidence

ORD record
ord-90e6db9965d34284b5873fe528e8caf2
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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