Triethylamine → HCID 18331414, compound

HRID 2270549Notes

Reaction equation

HRID 2270549 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:18]=2[C:19](O)=[O:20])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[C:18]([CH2:19][OH:20])=[CH:22][CH:23]=[C:24]([O:26][CH3:27])[N:25]=2)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18331433HCID 18331433, compound

Product 1

HCID 18331414HCID 18331414, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of the compound (300 mg) obtained in Example 452, triethylamine (101 mg) and tetrahydrofuran (8 ml), a tetrahydrofuran solution (1 ml) of ethyl chlorocarbonate (109 mg) was added under ice cooling and the resulting mixture was stirred at 0° C. for 15 min. The reaction mixture was filtered and a tetrahydrofuran solution (2 M, 0.8 ml) of lithium borohydride was added to the filtrate under ice cooling. The reaction mixture was stirred at 0° C. for 30 min and thereafter a 1 N aqueous sodium hydroxide solution was added under ice cooling. Further, the reaction mixture was stirred at 0° C. for 5 min and then ether and water were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:methylene chloride=1:10) to give 199 mg of the titled compound (yield, 69%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiona tetrahydrofuran solution (2 M, 0.8 ml) of lithium borohydride was added to the filtrate under ice cooling
  3. stirringThe reaction mixture was stirred at 0° C. for 30 min
  4. additiona 1 N aqueous sodium hydroxide solution was added under ice cooling
  5. stirringFurther, the reaction mixture was stirred at 0° C. for 5 min
  6. additionether and water were added
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:methylene chloride=1:10)

Sources & evidence

ORD record
ord-a8b48702f60743b19734d614699ae6e7
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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