Ethyl chloroformate → HCID 69585130, compound

HRID 2212436Notes

Reaction equation

HRID 2212436 reaction equation
[C:1]([O:4][CH2:5][O:6][C:7](=[O:28])[C:8]([NH:19][NH:20]C(OC(C)(C)C)=O)([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)(=[O:3])[CH3:2].Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>ClCCl>[C:1]([O:4][CH2:5][O:6][C:7](=[O:28])[C:8]([NH:19][NH2:20])([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:12]([O:17][C:5]([O:4][CH2:1][CH3:2])=[O:6])[CH:11]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 69585023HCID 69585023, compound

Product 1

HCID 69585130HCID 69585130, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold reaction mixture containing compound 103 (0.358 g, 0.9 mmol) and TEA (0.224 mL, 1.8 mmol) in dichloromethane (5 mL) was added ethyl chloroformate (0.18 mL, 1.8 mmol). The mixture was stirred at 0° C. for 30 min and then at room temperature for 1 h. After removal of solvent, 10% citric acid was added and 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. After removing the solvent under reduced pressure, the resulting residue was purified by reverse phase preparative HPLC to afford 208 mg of the title compound. 1H NMR (CD3OD, 400 MHz): 1.35 (t, 6H), 1.45 (s, 3H), 3.08 (dd, 2H), 3.80 (s, 3H), 4.28 (q, 4H), 5.83 (dd, 2H), 7.12–7.24 (m, 3H). MS (ESI) m/z 443.28 (M+H+).

Workup

  1. waitat room temperature for 1 h
  2. customAfter removal of solvent, 10% citric acid
  3. additionwas added
  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. customAfter removing the solvent under reduced pressure
  9. customthe resulting residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-6a93dde9465e4d60a90a561722e32cd3
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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